AMERICAN MEDICAL SECURITY GROUP INC
DEF 14A, 1999-04-13
HOSPITAL & MEDICAL SERVICE PLANS
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<PAGE>


                                  SCHEDULE 14A
                                 (RULE 14a-101)

                     INFORMATION REQUIRED IN PROXY STATEMENT
                            SCHEDULE 14A INFORMATION

          PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES
                    EXCHANGE ACT OF 1934 (AMENDMENT NO. ___)

Filed by the Registrant [ ]

Filed by a Party other than the Registrant [X]

Check the appropriate box:

[ ]   Preliminary Proxy Statement         [ ] Confidential, for Use 
                                              of the Commission Only
[X]   Definitive Proxy Statement              (as Permitted by Rule 14a-6(e)(2))

[ ]   Definitive Additional Materials

[ ]   Soliciting Material Pursuant to Rule 14(a)-11(c) or Rule 14a-12

                      AMERICAN MEDICAL SECURITY GROUP, INC.

                (Name of Registrant as Specified In Its Charter)

                               MERRILL CORPORATION

                   (Name of Person(s) Filing Proxy Statement,
                            if Other than Registrant)

Payment of Filing Fee (Check the appropriate box):

[X]   No fee required
[ ]   Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11

      1) Title of each class of securities to which transaction applies:
      2) Aggregate number of securities to which transaction applies:
      3) Per unit price or other underlying value of transaction
         computed pursuant to Exchange Act Rule 0-11 (set forth the
         amount on which the filing fee is calculated and state how it
         was determined):
      4) Proposed maximum aggregate value of transaction: 
      5) Total fee paid:

[ ]   Fee paid previously with preliminary materials.
[ ]   Check box if any part of the fee is offset as provided by Exchange
      Act Rule 0-11(a)(2) and identify the filing for which the offsetting
      fee was paid previously. Identify the previous filing by registration
      statement number, or the Form or Schedule and the date of its filing.

      1) Amount Previously Paid:
      2) Form, Schedule or Registration Statement No.:
      3) Filing Party:
      4) Date Filed:

<PAGE>
                                     [LOGO]
 
                               3100 AMS BOULEVARD
                              GREEN BAY, WI 54313
                                 (920) 661-1500
 
                                             April 14, 1999
 
To All Shareholders:
 
    You are cordially invited to attend the Company's 1999 Annual Meeting of
Shareholders on May 27, 1999, in Green Bay, Wisconsin.
 
    The Annual Meeting will begin promptly at 11:00 a.m. at the Radisson Inn
located at 2040 Airport Drive, Green Bay, Wisconsin.
 
    The official Notice of Annual Meeting, Proxy Statement and appointment of
proxy form are included with this letter. The matters listed in the Notice of
Annual Meeting are described in detail in the Proxy Statement.
 
    The vote of every shareholder is important to us. Please note that returning
your completed proxy will not prevent you from voting in person at the Annual
Meeting if you wish to do so. Your cooperation in promptly signing, dating and
returning your proxy will be greatly appreciated.
 
                                          Sincerely,
 
                                                       [SIGNATURE]
 
                                          Samuel V. Miller
                                          CHAIRMAN OF THE BOARD, PRESIDENT
                                          AND CHIEF EXECUTIVE OFFICER
<PAGE>
                                     [LOGO]
 
                    NOTICE OF ANNUAL MEETING OF SHAREHOLDERS
 
To the Holders of Common Stock
of American Medical Security Group, Inc.:
 
    The Annual Meeting of the Shareholders (the "Meeting") of American Medical
Security Group, Inc. (the "Company") will be held at the Radisson Inn located at
2040 Airport Drive, Green Bay, Wisconsin, on Thursday, May 27, 1999, at 11:00
a.m. local time, for the following purposes:
 
    1.  To elect three directors of the Company for terms expiring at the 2002
       Annual Meeting of Shareholders;
 
    2.  To consider and vote upon a proposal to amend the American Medical
       Security Group, Inc. Equity Incentive Plan to allow non-employee
       directors to participate in the Equity Incentive Plan and to make other
       amendments to the Equity Incentive Plan as described herein;
 
    3.  To consider and vote upon a proposal to approve the American Medical
       Security Group, Inc. Executive Annual Incentive Plan as described herein;
       and
 
    4.  To transact any other business as may properly come before the Meeting
       or any adjournment or postponement thereof.
 
    Only shareholders of record at the close of business on March 24, 1999, the
record date for the Meeting, are entitled to receive notice of and to vote at
the Meeting or any adjournment or postponement thereof.
 
    A copy of the Proxy Statement furnished in connection with the solicitation
of proxies by the Company's Board of Directors for use at the Meeting
accompanies this Notice.
 
    Shareholders who cannot attend in person are requested to complete and
return the enclosed proxy in the envelope provided. You may revoke your proxy at
any time prior to the voting thereof by advising the Secretary of the Company in
writing (by subsequent proxy or otherwise) of such revocation at any time before
it is voted.
 
               YOUR VOTE IS IMPORTANT. WHETHER OR NOT YOU PLAN TO
               ATTEND THE MEETING, PLEASE MARK, SIGN AND DATE THE
                     ENCLOSED PROXY AND RETURN IT PROMPTLY
                           IN THE ENVELOPE PROVIDED.
 
                                          By Order of the Board of Directors,
 
                                                   [SIGNATURE]
 
                                          Timothy J. Moore
                                          SECRETARY
 
Green Bay, Wisconsin
April 14, 1999
<PAGE>
                                     [LOGO]
 
                               3100 AMS BOULEVARD
                           GREEN BAY, WISCONSIN 54313
 
                            ------------------------
 
                                PROXY STATEMENT
                                      FOR
                         ANNUAL MEETING OF SHAREHOLDERS
                           TO BE HELD ON MAY 27, 1999
 
                            ------------------------
 
                            SOLICITATION AND VOTING
 
    This Proxy Statement is furnished in connection with the solicitation of
proxies by the Board of Directors of American Medical Security Group, Inc. (the
"Company" or "AMS") for use at the Annual Meeting of Shareholders (the
"Meeting") to be held at the Radisson Inn located at 2040 Airport Drive, Green
Bay, Wisconsin, on Thursday, May 27, 1999, at 11:00 a.m. local time, and at any
adjournment or postponement thereof. At the Meeting, shareholders of the Company
will consider and vote upon (i) the election of three directors of the Company
for terms expiring at the 2002 Annual Meeting of Shareholders; (ii) a proposal
to amend the American Medical Security Group, Inc. Equity Incentive Plan (the
"Equity Incentive Plan") to allow non-employee directors to participate in the
Equity Incentive Plan and to make other amendments as described herein; (iii) to
approve the American Medical Security Group, Inc. Executive Annual Incentive
Plan ("Annual Incentive Plan"); and (iv) such other business as may be properly
brought before the Meeting.
 
    Only holders of record of shares of common stock, no par value per share
("Common Stock"), of the Company at the close of business on March 24, 1999, the
record date for the Meeting, are entitled to receive notice of and to vote at
the Meeting. Shareholders will be entitled to one vote for each share of Common
Stock held. On March 24, 1999, there were issued and outstanding 16,653,262
shares of Common Stock.
 
    When you sign and return the enclosed appointment of proxy form, shares of
the Common Stock represented thereby will be voted (i) FOR the nominees for
directors named in this Proxy Statement, (ii) FOR the adoption of the proposed
amendments to the Equity Incentive Plan, and (iii) FOR the adoption of the
Annual Incentive Plan, unless otherwise indicated on the proxy form. The Board
of Directors expects all nominees for director to be available for election. In
the event that any nominee for director is not available to serve, the proxy
holders may vote for a substitute designated by the Board of Directors of the
Company. Returning your completed proxy form will not prevent you from voting in
person at the Meeting should you be present and wish to do so. You may revoke
your proxy at any time before it is voted by advising the Secretary of the
Company of such revocation in writing (by subsequent proxy or otherwise).
 
    The Company knows of no other matters to come before the Meeting. If any
other matters properly come before the Meeting, it is the intention of the
persons acting pursuant to the accompanying appointment of proxy form to vote
the shares represented thereby in accordance with their best judgment.
 
    A majority of the votes entitled to be cast by the shares entitled to vote,
represented in person or by proxy, will constitute a quorum at the Meeting.
Abstentions, shares for which authority is withheld to vote
 
                                       1
<PAGE>
for director nominees, and broker non-votes (i.e., proxies from brokers or
nominees indicating that such persons have not received instructions from the
beneficial owners or other persons entitled to vote shares as to a matter with
respect to which the brokers or nominees do not have discretionary power to
vote) will be considered present for purposes of establishing a quorum.
 
    Directors are elected by a plurality of the votes cast by the shares
entitled to vote in the election at a shareholders' meeting at which a quorum is
present. "Plurality" means that the individuals who receive the largest number
of votes are elected as directors up to the maximum number of directors to be
chosen in the election. Therefore, any shares not voted, whether by withheld
authority, broker non-vote or otherwise, have no effect in the election of
directors except to the extent that the failure to vote for an individual
results in another individual receiving a larger number of votes.
 
    If a quorum exists, the affirmative vote of a majority of the votes cast
will be required for approval of the adoption of the proposed amendments to the
Equity Incentive Plan and for approval of the adoption of the Annual Incentive
Plan, provided that the total votes cast on each proposal represents over 50% of
the shares entitled to vote thereon. Because abstentions and broker non-votes
are not considered votes cast, neither will have an effect on the vote so long
as enough votes are cast to satisfy the 50% requirement set forth above. The
Inspectors of Election appointed under the authority of the Board of Directors
will count the votes and ballots at the Annual Meeting.
 
    The expense of preparing, printing, and mailing this Proxy Statement and the
proxies solicited hereby will be borne by the Company. Officers and other
employees of the Company may solicit proxies by personal interview, telephone
and facsimile, in addition to the use of the mails, but will receive no
additional compensation for such activities. The Company also has made
arrangements with brokerage firms, banks, nominees and other fiduciaries to
forward proxy solicitation materials for shares of the Common Stock held of
record by them to the beneficial owners of such shares. The Company will
reimburse them for reasonable out-of-pocket expenses.
 
    The Annual Report to Shareholders for the year ended December 31, 1998, the
Notice of the Meeting, this Proxy Statement and the accompanying appointment of
proxy form were first mailed to shareholders on or about April 14, 1999.
 
                    SECURITY OWNERSHIP OF CERTAIN BENEFICIAL
                             OWNERS AND MANAGEMENT
 
    The following table sets forth information regarding the beneficial
ownership (as that term is defined in Rule 13d-3 under the Securities Exchange
Act of 1934 (the "Exchange Act")) of shares of Common Stock by (i) each person
or entity known to the Company to own beneficially more than 5% of the shares of
the Common Stock outstanding, (ii) each nominee for director and director of the
Company, (iii) each executive officer of the Company named in the Summary
Compensation Table below, and (iv) all directors and executive officers of the
Company as a group. Unless otherwise indicated, each shareholder listed below
has sole voting and dispositive power with respect to shares of Common Stock
beneficially owned. Amounts are as of March 24, 1999, for nominees for director,
directors, and executive officers. Amounts for 5% shareholders (other than Mr.
Miller) are as disclosed in reports regarding such ownership filed with the
Securities and Exchange Commission (the "SEC") in accordance with Sections 13(d)
or 13(g) of the Exchange Act.
 
                                       2
<PAGE>
 
<TABLE>
<CAPTION>
                                                                                    NUMBER OF SHARES
                                                                                      BENEFICIALLY       PERCENT OF
NAME AND ADDRESS                                                                        OWNED(1)            CLASS
- --------------------------------------------------------------------------------  --------------------  -------------
<S>                                                                               <C>                   <C>
Blue Cross & Blue Shield United of Wisconsin....................................         6,309,525             37.9%
  1515 N. RiverCenter Drive
  Milwaukee, WI 53212
Heartland Advisors, Inc.(2).....................................................         1,340,000              8.0
  790 North Milwaukee Street
  Milwaukee, WI 53202
Oppenheimer Capital(3)..........................................................         1,110,016              6.7
  Oppenheimer Tower, World Financial Center
  New York, NY 10281
Samuel V. Miller (4)............................................................           974,175              5.5
  3100 AMS Boulevard
  Green Bay, WI 54313
Wallace J. Hilliard(5)..........................................................           934,500              5.4
  P. O. Box 12146
  Green Bay, WI 54307-2146
Roger H. Ballou.................................................................                --               --
W. Francis Brennan..............................................................             3,000                *
James C. Hickman................................................................               200                *
William R. Johnson..............................................................             4,500                *
Eugene A. Menden................................................................             1,500                *
Michael T. Riordan                                                                              --               --
Frank L. Skillern...............................................................                --               --
J. Gus Swoboda..................................................................             1,500                *
Edward R. Skoldberg.............................................................            32,763                *
Gary D. Guengerich..............................................................            42,988                *
Timothy J. Moore................................................................            16,386                *
Scott B. Westphal...............................................................            26,934                *
Thomas R. Hefty (4)(6)..........................................................           176,223              1.0
Roger A. Formisano (4)(6).......................................................             6,450                *
All directors and executive officers as a group: 16 persons (6).................         1,110,218              6.3
</TABLE>
 
- ------------------------
 
 *  Amount represents less than 1% of the total shares of the Common Stock
    issued and outstanding.
 
(1) Includes the following number of shares which the individual has the right
    to acquire within 60 days of March 24, 1999, upon the exercise of stock
    options: Mr. Miller, 972,175 shares; Mr. Hilliard, 530,000 shares; Mr.
    Skoldberg, 32,763 shares; Mr. Guengerich, 32,788 shares; Mr. Moore, 16,386
    shares; Mr. Westphal, 19,727 shares; Mr. Hefty, 155,543 shares; and all
    directors and officers as a group, 1,079,301 shares.
 
(2) Heartland Advisors, Inc. has sole voting power with respect to 623,600
    shares and sole dispositive power with respect to 1,340,000 shares
    beneficially owned.
 
(3) Oppenheimer Capital has shared voting and dispositive power with respect to
    all shares beneficially owned.
 
(4) Includes the following shares owned jointly with such person's spouse, with
    respect to which such person shares voting power and dispositive power: Mr.
    Miller, 2,000 shares; Mr. Hefty, 5,000 shares; Mr. Formisano, 4,650 shares.
 
(5) Mr. Hilliard has voting and dispositive power with respect to shares
    beneficially owned as follows: sole voting power, 765,000 shares; shared
    voting power, 169,500 shares; sole dispositive power, 530,000
 
                                       3
<PAGE>
    shares; and shared dispositive power, 404,500 shares. On March 30, 1999, Mr.
    Hilliard entered into an Option Surrender Agreement with the Company
    pursuant to which he surrendered stock options to purchase 530,000 shares of
    Company Common Stock, which are included in shares beneficially owned by Mr.
    Hilliard in this table. See "Certain Transactions--Other Agreements."
 
(6) Although no longer officers of the Company, Messrs. Hefty and Formisano are
    required to be listed in this table and the Summary Compensation Table below
    in accordance with Exchange Act reporting requirements. However, because
    they were not executive officers at March 24, 1999, they are not included
    under "all directors and executive officers as a group" in this table.
 
    Blue Cross & Blue Shield United of Wisconsin ("Blue Cross") owns 37.9% of
the issued and outstanding shares of the Common Stock. James C. Hickman, a
director of the Company, is also a director of Blue Cross. Mr. Hickman and two
other Company directors, Eugene A. Menden and William R. Johnson, are directors
of United Wisconsin Services (as defined in "Certain Transactions" below). Blue
Cross beneficially owns more than 10% of the common stock of United Wisconsin
Services. It is anticipated that Blue Cross will vote its shares of Common Stock
(i) in favor of each of the nominees for director, (ii) in favor of the
amendments to the Equity Incentive Plan, and (iii) in favor of the Annual
Incentive Plan.
 
                                       4
<PAGE>
                         ITEM 1--ELECTION OF DIRECTORS
 
    Three directors are to be elected at the Annual Meeting to serve three year
terms expiring at the 2002 Annual Meeting and until their respective successors
are duly elected and qualified. The names of the persons nominated by the Board
of Directors and the continuing Board members are set forth below, along with
additional information regarding such persons. Each nominee is presently serving
as a director of the Company.
 
    The election shall be determined by a plurality of the votes cast. Unless
otherwise specified, the shares of Common Stock represented by the proxies
solicited hereby will be voted in favor of the election of the nominees
described below. The three nominees have indicated that they are able and
willing to serve as directors. However, if any of the nominees should be unable
to serve, an eventuality which management does not contemplate, it is intended
that the proxies will vote for the election of such other person or persons as
the Board of Directors of the Company may recommend.
 
    THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE "FOR" THE NOMINEES FOR
DIRECTORS
 
                         NOMINEES STANDING FOR ELECTION
 
       NOMINEES FOR ELECTION AT THIS MEETING WITH TERMS EXPIRING IN 2002
 
<TABLE>
<CAPTION>
                              DIRECTOR
                                SINCE                     PRINCIPAL OCCUPATION DURING PAST FIVE YEARS
                             -----------  ---------------------------------------------------------------------------
<S>                          <C>          <C>
 
Roger H. Ballou                    1998   Mr. Ballou has been the Chairman of the Board and Chief Executive Officer
Age: 48                                   of Global Vacation Group since March 1998. Immediately prior to that time,
                                          Mr. Ballou served as a senior advisor to Thayer Capital Partners. Between
                                          May 1995 and September 1997, Mr. Ballou served as Vice Chairman and Chief
                                          Marketing Officer and then as President and Chief Operating Officer of
                                          Alamo Rent-a-Car. From 1989 to 1995, Mr. Ballou was President of the Travel
                                          Services Group of American Express Company.
 
W. Francis Brennan                 1998   Mr. Brennan is a retired Executive Vice President of UNUM Corporation, a
Age: 62                                   life and health insurance company, where he served on the boards of UNUM's
                                          insurance affiliates in the United States, Canada, the United Kingdom and
                                          Japan. He joined UNUM in 1984 and retired in 1995. He is a director of
                                          Margent Group, Inc., a reinsurance holding company with operations in the
                                          United States, the United Kingdom and Bermuda.
 
J. Gus Swoboda                     1998   Mr. Swoboda is a retired Senior Vice President of Wisconsin Public Service
Age: 63                                   Corporation, an electric and gas utility, where he also held various other
                                          senior management positions. He joined Wisconsin Public Service in 1959 and
                                          retired in 1997. He is Chairman of the Board of Directors of First Northern
                                          Capital Corp., a publicly traded financial institution.
</TABLE>
 
                                       5
<PAGE>
                              CONTINUING DIRECTORS
 
               DIRECTORS WHOSE PRESENT TERMS CONTINUE UNTIL 2000
 
<TABLE>
<CAPTION>
                              DIRECTOR
                                SINCE                     PRINCIPAL OCCUPATION DURING PAST FIVE YEARS
                             -----------  ---------------------------------------------------------------------------
<S>                          <C>          <C>
 
James C. Hickman                   1991   Mr. Hickman has been an Emeritus Professor and Emeritus Dean of the School
Age: 71                                   of Business at the University of Wisconsin-Madison ("UW School of
                                          Business") since July 1993. He was a Professor at the UW School of Business
                                          from 1972 to 1993, serving as Dean of the UW School of Business from 1985
                                          to 1990. He is a director of United Wisconsin Services, Blue Cross, and
                                          Century Investment Management Company.
 
William R. Johnson                 1993   Mr. Johnson has been Chairman of Johansen Capital Associates, Inc., a
Age: 72                                   financial and investment consulting firm, since 1986. He is a director of
                                          United Wisconsin Services and Campbell, Newman, Pottinger & Associates, an
                                          investment consulting firm.
 
Frank L. Skillern                  1998   Mr. Skillern has been Chairman of the Board of Directors of American
Age: 62                                   Express Centurion Bank, a consumer bank located in Salt Lake City, Utah,
                                          since February 1999. He was Chief Executive Officer of American Express
                                          Centurion Bank from 1996 to February 1999, and a director of American
                                          Express Centurion Bank since 1991. From 1994 to 1996 he was President,
                                          Consumer Card Group, USA, American Express Travel Related Services Company
                                          ("TRS"), having served as an Executive Vice President of TRS for the prior
                                          two years.
</TABLE>
 
               DIRECTORS WHOSE PRESENT TERMS CONTINUE UNTIL 2001
 
<TABLE>
<CAPTION>
                              DIRECTOR
                                SINCE                     PRINCIPAL OCCUPATION DURING PAST FIVE YEARS
                             -----------  ---------------------------------------------------------------------------
<S>                          <C>          <C>
 
Eugene A. Menden                   1991   Mr. Menden is a retired Vice President and Director of Marquette Medical
Age: 68                                   Systems, Inc. (formerly known as Marquette Electronics, Inc.), a
                                          manufacturer of medical electronic products, where he also held various
                                          other senior management positions in his over 20-year career with the
                                          company. He is also a director of United Wisconsin Services.
 
Samuel V. Miller                   1998   Mr. Miller has been Chairman of the Board, President and Chief Executive
Age: 53                                   Officer of the Company since September 1998. He was an Executive Vice
                                          President of the Company from 1995 to 1998 and also served as President and
                                          Chief Executive Officer of American Medical Security Holdings, Inc. since
                                          1996. During 1994 to 1995, Mr. Miller was a member of the executive staff
                                          planning group with the Travelers Group, serving as Chairman and Group
                                          Chief Executive of National Benefit Insurance Company and Primerica
                                          Financial Services Ltd. of Canada. Prior to 1994, Mr. Miller spent 10 years
                                          as President and Chief Executive Officer of American Express Life Assurance
                                          Company.
</TABLE>
 
                                       6
<PAGE>
<TABLE>
<CAPTION>
                              DIRECTOR
                                SINCE                     PRINCIPAL OCCUPATION DURING PAST FIVE YEARS
                             -----------  ---------------------------------------------------------------------------
<S>                          <C>          <C>
Michael T. Riordan                 1998   Mr. Riordan was President and Chief Operating Officer of Fort James
Age: 48                                   Corporation, a consumer products company, from 1997 to August 1998. He was
                                          Chairman and Chief Executive Officer of Fort Howard Corporation from 1996
                                          to 1997, and President of Fort Howard Corporation from 1992 to 1996. Fort
                                          Howard Corporation merged with James River Corporation in 1997 to become
                                          Fort James Corporation. He is also a director of the Dial Corporation.
</TABLE>
 
MEETINGS OF THE BOARD OF DIRECTORS AND COMMITTEES OF THE BOARD OF DIRECTORS
 
    In fiscal 1998, the Board of Directors held five meetings. During 1998, each
director attended at least 80% of these meetings and the meetings of the
committees of the Board of Directors of which he was a member. The Board of
Directors has standing Audit, Compensation, Finance, and Executive Committees.
 
    The Audit Committee selects and engages the Company's independent public
accountants; reviews the scope and results of the Company's audits with the
independent auditors; and reviews the adequacy and effectiveness of the
Company's internal auditing, accounting, and financial controls with the
independent auditors and the Company's financial and accounting personnel. The
Audit Committee also reviews the audited financial statements of the Company and
the auditors' reports and management letter with the independent public
accountants. In addition, the Audit Committee reviews and evaluates
related-party transactions and conflict of interest statements, and discharges
certain other responsibilities of the Board of Directors when so instructed by
the Board. The Audit Committee is composed entirely of outside directors. The
members of the Audit Committee are Messrs. Menden (Chairman), Hickman, Brennan,
and Swoboda. The Audit Committee held three meetings during 1998.
 
    The Compensation Committee (f/k/a the Management Review Committee) evaluates
the performance of the Company's executive officers; determines the compensation
of the executive officers; reviews the compensation of other key employees; acts
as the nominating committee for directors; makes recommendations to the Board of
Directors regarding the types, methods and levels of director compensation;
administers the Company's equity-based compensation plans; administers the other
compensation plans for executive officers and directors; and discharges certain
other responsibilities of the Board of Directors when so instructed by the
Board. The Compensation Committee will consider a nominee for election to the
Board of Directors recommended by a shareholder if the shareholder submits the
nomination in compliance with the requirements of the Company's Bylaws relating
to nominations by shareholders. The Compensation Committee is composed entirely
of outside directors. The members of the Compensation Committee are Messrs.
Riordan (Chairman), Brennan, Ballou, and Skillern. The Compensation Committee
held five meetings during 1998.
 
    The Finance Committee approves investment policies and plans; approves the
investment of funds of the Company; consults with management regarding the
Company's capital structure and material transactions involving real estate,
accounts receivable and other assets; monitors the amounts and types of
insurance carried by the Company; monitors the Company's relationship with its
lenders; and discharges certain other responsibilities of the Board of Directors
when so instructed by the Board. The members of the Finance Committee are
Messrs. Johnson (Chairman), Menden, Miller, and Skillern. The Finance Committee
held three meetings during 1998.
 
    The Executive Committee discharges certain responsibilities of the Board of
Directors when so instructed by the Board. When the Board of Directors is not in
session, the Executive Committee may exercise all of the powers and authority of
the full Board in the management of the business and affairs of the Company to
the extent allowed by the Wisconsin Business Corporation Law. The Executive
Committee did not hold any meetings during 1998. The members of the Executive
Committee are Messrs. Miller (Chairman), Ballou, Hickman, and Riordan.
 
                                       7
<PAGE>
COMPENSATION OF DIRECTORS
 
    Directors who are officers or employees of the Company do not receive any
compensation for service as members of the Board of Directors or committees of
the Board. A director who is not an officer or employee of the Company receives
an $18,000 annual fee and $1,000 per day for attendance at Board or committee
meetings. In addition, each committee chairman receives a $3,600 annual fee and
other committee members receive a $1,800 annual fee. The Company also reimburses
directors for their travel expenses in connection with their attendance at Board
and committee meetings. The payment of a director's annual fees may be deferred
by any director at such director's election pursuant to the Company's Deferred
Compensation Plan for Directors until the earlier of (i) the date of termination
of such director's service as a non-employee director, (ii) the date specified
by such director in his deferred election form, or (iii) the date of such
director's death.
 
    Pursuant to the 1995 Director Stock Option Plan of the Company, each
non-employee director has been granted, in connection with his service as a
director, an option to purchase 5,000 shares of Common Stock at an exercise
price equal to the fair market value of the Common Stock on the date of such
grant. Subject to approval of amendments to the Equity Incentive Plan by
shareholders at the Meeting, non-employee directors will be eligible to receive
benefits under the Amended and Restated Equity Incentive Plan. See "Item
2--Approval of Amendments to American Medical Security Group, Inc. Equity
Incentive Plan."
 
NOMINATIONS FOR DIRECTORS BY SHAREHOLDERS
 
    The Board of Directors will consider a nominee for election to the Board
recommended by a shareholder if the shareholder submits the nomination in
compliance with the requirements of the Company's Bylaws relating to nominations
by shareholders. Article II, Section 2.01(B) of the Company's Bylaws provides
that if a shareholder desires to make a nomination for the election of directors
at an annual meeting, he or she must give timely written notice of the
nomination to the Secretary of the Company. Notice is timely if received by the
Secretary at the Company's principal office in the year of the applicable annual
meeting not less than 60 days nor more than 90 days prior to the date on which
the Company first mailed its proxy materials for the prior year's annual meeting
of shareholders. The annual meeting of shareholders is generally held on the
last Thursday in May. The notice must set forth the shareholder's name and
address as they appear on the Company's books; the class and number of shares of
Common Stock beneficially owned by such shareholder; a representation that such
shareholder is a holder of record of shares entitled to vote at the meeting and
intends to appear at the meeting, in person or by proxy, to make the nomination;
the name and residential address of the nominee; a description of all
arrangements or understandings between the shareholder and the nominee (and any
other person or persons) pursuant to which the nomination is to be made; the
written consent of the nominee to serve, if elected; and certain other
information. The notice must be signed by the shareholder of record who intends
to make the nomination (or his or her duly authorized proxy or other
representative) and must bear the date of signature of such shareholder or
representative. Article II, Section 2.01(B) of the Bylaws provides that notices
with respect to any nomination for a Board election to be held at any special
meeting must contain all the information set forth above and must be received by
the Secretary of the Company not earlier than 90 days and not later than the
later of 60 days prior to the special meeting or ten days after notice of such
meeting is first given to shareholders. Shareholders wishing to submit a
nomination should review the Bylaw requirement regarding nominations by
shareholders and should communicate with the Secretary of the Company at
American Medical Security Group, Inc., 3100 AMS Boulevard, Green Bay, Wisconsin
54313, for further information.
 
                                       8
<PAGE>
                       ITEM 2--APPROVAL OF AMENDMENTS TO
          AMERICAN MEDICAL SECURITY GROUP, INC. EQUITY INCENTIVE PLAN
 
    In fiscal 1993, the Board of Directors of the Company, then known as United
Wisconsin Services, Inc., adopted the United Wisconsin Services, Inc. Equity
Incentive Plan (the "Equity Incentive Plan") effective as of February 24, 1993,
upon ratification by an affirmative vote of a majority of shares of Common Stock
at the 1993 Annual Meeting of Shareholders. The Equity Incentive Plan was
designed to permit the grant of non-qualified stock options ("NQSOs"), incentive
stock options ("ISOs"), stock appreciation rights ("SARs"), restricted stock,
performance units, and performance shares to officers and employees of the
Company. The purpose of the Equity Incentive Plan was to promote the success and
enhance the value of the Company by linking the personal interests of
participants to those of the Company's shareholders, and by providing
participants with an incentive for outstanding performance. The Equity Incentive
Plan was further intended to provide flexibility to the Company in its ability
to motivate, attract, and retain the services of participants upon whose
judgment, interest, and special effort the successful conduct of its operation
is dependent.
 
    As described in "Certain Transactions" below, the Company engaged in a
corporate reorganization and Spin-off (as hereinafter defined) of certain of its
businesses effective as of September 25, 1998 (the "Reorganization Date"). See
"Certain Transactions" and "Compensation Committee Report on Executive
Compensation--Business Considerations." In connection with the Spin-off the
Company changed its name to "American Medical Security Group, Inc." and changed
the name of the Equity Incentive Plan to the "American Medical Security Group,
Inc. Equity Incentive Plan." Accordingly, the Equity Incentive Plan remains in
effect in substantially the same form as prior to the Reorganization Date.
 
    As part of its continuous evaluation of the appropriateness and adequacy of
the Company's executive compensation program, the Compensation Committee of the
Board of Directors (the "Compensation Committee") determined in fiscal 1998
that, since only 29,000 shares were available for future grant under the
Company's 1995 Director Stock Option Plan, the Equity Incentive Plan should be
amended to include grants to non-employee directors as well as employees. The
Compensation Committee came to that decision, in part, in order to continue its
efforts to improve the links between incentives, the Company's strategic
objectives, and the enhancement of shareholder value. Accordingly, the
Compensation Committee recommended and, on March 15, 1999, the Board approved,
various amendments to the Equity Incentive Plan (as amended, the "Amended and
Restated Equity Incentive Plan") to make directors eligible for grants
thereunder and to make certain other changes, as described under "Proposed
Amendments" below. The proposed amendments to the Equity Incentive Plan do NOT
increase the number of shares available for issuance under the Amended and
Restated Equity Incentive Plan. As of the April 1, 1999, of the 4,000,000 shares
authorized for issuance pursuant to the Equity Incentive Plan, 312,180 shares
had been issued, 1,953,893 shares were subject to outstanding awards (all of
which were nonqualified stock options) and 1,733,927 shares were available for
additional awards. On April 1, 1999, the closing price of the Common Stock on
the New York Stock Exchange was $14.69.
 
    Adoption of certain of the amendments to the Equity Incentive Plan is
subject to approval by the Company's shareholders at the 1999 Annual Meeting.
However, if shareholder approval is not obtained, the Equity Incentive Plan will
remain in effect.
 
    THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE "FOR" APPROVAL OF THE
AMENDMENTS TO THE EQUITY INCENTIVE PLAN.
 
    A copy of the Amended and Restated Equity Incentive Plan is attached hereto
as Appendix A. The following description of certain provisions of the Equity
Incentive Plan is qualified in its entirety by reference to the complete text
set forth in Appendix A.
 
                                       9
<PAGE>
PRINCIPAL TERMS OF THE AMENDED AND RESTATED EQUITY INCENTIVE PLAN
 
    ADMINISTRATION.  The Amended and Restated Equity Incentive Plan will be
administered by the Compensation Committee or by any other committee appointed
by the Board of Directors of the Company consisting of not less than two
directors who are not employees of the Company.
 
    ELIGIBILITY.  Persons eligible to participate in the Amended and Restated
Equity Incentive Plan include all directors and all full-time, active employees
of the Company, its subsidiaries and affiliates, as determined by the
Compensation Committee. Subject to the provisions of the Amended and Restated
Equity Incentive Plan, the Compensation Committee may, from time to time, select
from all eligible participants those to whom awards shall be granted and shall
determine the nature and amount of each award.
 
    PLAN FEATURES.  The Amended and Restated Equity Incentive Plan authorizes
the issuance of up to 4,000,000 shares of Company Common Stock pursuant to the
grant or exercise of stock options, stock appreciation rights ("SARs"),
restricted stock, performance units, and performance shares. The 4,000,000
shares may be either authorized but unissued or reacquired (treasury) shares of
Company Common Stock. The maximum number of shares with respect to which awards
may be made to any participant annually shall not exceed 250,000 shares. No
participant may be granted performance units in any one calendar year that when
payable would exceed $3,000,000. If any award granted under the Amended and
Restated Equity Incentive Plan is canceled, terminates, expires, or lapses for
any reason, any shares of Company Common Stock subject to such award again shall
be available for the grant of an award under the Amended and Restated Equity
Incentive Plan.
 
    As indicated above, several types of stock-related grants can be made under
the Amended and Restated Equity Incentive Plan. A summary of the grants is set
forth below:
 
    STOCK OPTIONS.  The Amended and Restated Equity Incentive Plan authorizes
the Compensation Committee to grant options to purchase Company Common Stock at
an exercise price which cannot be less than 100% of the fair market value of
such stock on the date of the grant. The Amended and Restated Equity Incentive
Plan permits optionees to pay the exercise price of options in cash, shares of
Company Common Stock (valued at its fair market value on the date of exercise),
or a combination thereof. As noted above, the Compensation Committee may grant
ISOs, NQSOs, or a combination thereof. The principal difference between ISOs and
NQSOs is their tax treatment. See "--Federal Income Tax Consequences."
 
    SARS.  The Amended and Restated Equity Incentive Plan authorizes the
Compensation Committee to grant SARs either in conjunction with all or part of
any stock option granted under the Amended and Restated Equity Incentive Plan or
independently of any option. Subject to the limits noted in "Plan Features"
above, the Compensation Committee shall have complete discretion in determining
the number of SARs granted to each participant. An SAR entitles the holder to
receive, upon exercise, the excess of the fair market value of a specified
number of shares of Company Common Stock at the time of exercise over the grant
price. Such amount will be paid to the holder in cash, shares of Company Common
Stock (valued at its fair market value on the date of exercise), or a
combination thereof, as the Compensation Committee may determine.
 
    RESTRICTED STOCK.  The Amended and Restated Equity Incentive Plan authorizes
the Compensation Committee to grant restricted stock to individuals with such
restriction periods as the Compensation Committee may designate. The
Compensation Committee may, prior to granting shares of restricted stock,
designate certain participants as "Covered Employees" upon determining that such
participants are or are expected to be "covered employees" within the meaning of
Section 162(m)(3) of the Internal Revenue Code (the "Code"), and will provide
that restricted stock awards to those Covered Employees cannot vest unless
applicable performance goals established by the Compensation Committee within
the time period prescribed by Section 162(m) of the Code are satisfied. These
performance goals must be based on the attainment of specified levels relating
to one or more of the following business criteria measured on an absolute basis
or in terms of growth or reduction: net income (pre-tax or after-tax and with
adjustments as
 
                                       10
<PAGE>
stipulated), earnings per share, return on equity, return on assets, return on
tangible book value, operating income, earnings before depreciation, interest,
taxes and amortization (EBDITA), loss ratio, expense ratio, increase in stock
price, total shareholder return, economic value added, and operating cash flow.
Performance goals based on the foregoing factors are hereinafter referred to as
"Performance Goals." With respect to Covered Employees, the Performance Goals
shall be objective performance goals satisfying the requirements for
"performance-based compensation" within the meaning of Section 162(m)(4) of the
Code and shall be established by the Compensation Committee within the time
prescribed by Section 162(m) of such Code and related regulations. With respect
to participants who are not Covered Employees, the Compensation Committee may
establish other subjective or objective Performance Goals, including individual
goals, it deems appropriate. The provisions of restricted stock awards
(including any applicable performance goals) need not be the same with respect
to each participant. Restricted stock may not be sold, transferred, pledged,
assigned or otherwise encumbered. Other than these restrictions on transfer, and
any other restrictions the Compensation Committee may impose, the participant
will have all the rights of a holder of stock holding the class or series of
stock that is the subject of the restricted stock award.
 
    PERFORMANCE UNITS AND PERFORMANCE SHARES.  The Amended and Restated Equity
Incentive Plan authorizes the Compensation Committee to grant performance units
and performance shares. The same conditions as noted in the preceding paragraph
with respect to awards to "Covered Employees" also apply to any grant of
performance units or performance shares to such employees. Subject to the limits
noted in "Plan Features" above, the Compensation Committee shall have complete
discretion in determining the number of performance units and performance shares
granted to each participant. Each performance unit shall have an initial value
that is established by the Compensation Committee at the time of grant. Each
performance share shall have an initial value equal to the fair market value of
a share of Company Common Stock on the date of grant. The Compensation Committee
shall set Performance Goals in its discretion which, depending on the extent to
which they are met, will determine the number and/or value of performance units
and performance shares that will be paid out to participants. The time period
during which the Performance Goals must be met (the "Performance Period") shall,
in all cases, exceed six months in length. After the Performance Period has
ended, the holder of performance units or performance shares shall be entitled
to receive a payout on the number of performance units or performance shares
earned by the participant over the Performance Period, to be determined as a
function of the extent to which the corresponding Performance Goals have been
achieved. Payment of earned performance units or performance shares shall be
made in a single lump sum, within 45 days following the close of the applicable
Performance Period. The Compensation Committee, in its sole discretion, may pay
earned performance units or performance shares in the form of cash, shares of
Company Common Stock (valued at its fair market value on the date of exercise),
or a combination thereof, which have an aggregate fair market value equal to the
value of the earned performance units or performance shares at the close of the
applicable Performance Period.
 
    The Compensation Committee will have the authority to determine the
participants to whom and the time or times at which performance units shall be
awarded, the number of performance units to be awarded to any participant, the
duration of the award cycle, and any other terms and conditions of an award.
 
    AMENDMENT AND DISCONTINUANCE.  The Amended and Restated Equity Incentive
Plan may be terminated, amended, or modified by the Compensation Committee, with
the approval of the Board of Directors, but no termination, amendment, or
modification may adversely affect in any material way any award previously
granted under the Amended and Restated Equity Incentive Plan, without the
written consent of the affected participant. Future amendments to the Amended
and Restated Equity Incentive Plan will not require the approval of shareholders
except to the extent required by law or regulatory requirements.
 
    CHANGES IN CAPITALIZATION; CHANGE IN CONTROL.  The Amended and Restated
Equity Incentive Plan provides that, in the event of any merger, reorganization,
consolidation, recapitalization, separation,
 
                                       11
<PAGE>
liquidation, stock dividend, split-up, share combination, or other change in the
corporate structure of the Company affecting the shares of Company Common Stock,
the number of shares of Company Common Stock which may be delivered under the
Plan, and the number and/or price of shares subject to outstanding options,
SARs, and restricted stock granted under the Amended and Restated Equity
Incentive Plan shall be adjusted as determined by the Compensation Committee in
order to prevent dilution or enlargement of rights. The Amended and Restated
Equity Incentive Plan also provides that in the event of a Change in Control (as
defined in the Amended and Restated Equity Incentive Plan) of the Company (a)
any and all options and SARs granted under the Amended and Restated Equity
Incentive Plan will become immediately exercisable; (b) any restriction periods
and restrictions imposed on restricted shares will lapse, and within ten
business days after the occurrence of a Change in Control, the stock
certificates representing shares of restricted stock, without any restrictions
or legend thereon, shall be delivered to the applicable participants; (c) the
target value attainable under all performance units and performance shares shall
be deemed to have been fully earned for the entire Performance Period as of the
effective date of the Change in Control, and shall be paid out in cash to
participants within 30 days following the effective date of the Change in
Control; provided, however, that there shall not be an accelerated payout with
respect to performance units or performance shares which were granted less than
six months prior to the effective date of the Change in Control; and (d) the
Compensation Committee shall have the authority to make any modifications to the
Awards as determined by the Compensation Committee to be appropriate before the
effective date of the Change in Control.
 
PROPOSED AMENDMENTS
 
    As noted above, the Compensation Committee revised the Amended and Restated
Equity Incentive Plan in several respects for the purpose of permitting grants
under the Amended and Restated Equity Incentive Plan to be made to directors as
well as officers and employees. Accordingly, several sections, including Section
2(o) defining "Employee," Section 2(t) defining "Insider," Section 2(x) defining
"Participant," Section 2(z) defining "Performance Unit," and Section 2(aa)
defining "Performance Share" have been modified, and Sections 6.10 ("Exercise of
Options With Respect to Directors"), 7.11 ("Exercise of SARs With Respect to
Directors"), 8.11 ("Restricted Stock Granted to Directors"), and 9.7
("Performance Units/Shares Granted to Directors") have been added to give the
Compensation Committee full discretion with respect to the rules in any award to
directors with respect to vesting and exercisability upon the director's
cessation of service for whatever reason. In addition, as described above, the
Amended and Restated Equity Incentive Plan has been revised to provide for
material terms of performance goals in connection with awards of restricted
stock, performance shares and performance units to participants designated as
"covered employees" within the meaning of Section 162(m)(3) of the Code. To add
flexibility under the terms of the Amended and Restated Equity Incentive Plan,
absent any other impediment, the Amended and Restated Equity Incentive Plan also
has been revised to provide that it may remain in effect until all of the shares
available under the Amended and Restated Equity Incentive Plan have been used.
However, to the extent required by the Code, no ISO may be granted on or after
February 24, 2003. Further, several minor, technical, corrective revisions have
been made to various provisions, including certain definitions.
 
CERTAIN FEDERAL INCOME TAX CONSEQUENCES
 
    The following is a brief summary of the Company's understanding of the
principal federal income tax consequences of grants made under the Amended and
Restated Equity Incentive Plan based upon the applicable provisions of the Code
in effect on the date hereof. The laws governing the tax aspects of awards are
highly technical and such laws are subject to change.
 
    NQSOS AND SARS.  Upon the grant of a nonqualified option (with or without an
SAR), the optionee will not recognize any taxable income and the Company will
not be entitled to a deduction. Upon the exercise of such an option or SAR, the
excess of the fair market value of the shares acquired on the exercise of the
option over the option price (the "spread"), or the consideration paid to the
optionee upon exercise of the
 
                                       12
<PAGE>
SAR, will constitute compensation taxable to the optionee as ordinary income.
The Company, in computing its federal income tax, will generally be entitled to
a deduction in an amount equal to the compensation taxable to the optionee.
 
    ISOS.  An optionee will not recognize taxable income on the grant or
exercise of an ISO. However, the spread at exercise will constitute an item
includible in alternative minimum taxable income, and thereby may subject the
optionee to the alternative minimum tax. Such alternative minimum tax may be
payable even though the optionee receives no cash upon the exercise of his or
her ISO with which to pay such tax.
 
    Upon the disposition of shares of stock acquired pursuant to the exercise of
an ISO after the later of (i) two years from the date of grant of the ISO or
(ii) one year after the transfer of the shares to the optionee (the "ISO Holding
Period"), the optionee will recognize long-term capital gain or loss, as the
case may be, measured by the difference between the stock's selling price and
the exercise price. The Company is not entitled to any tax deduction by reason
of the grant or exercise of an ISO, or by reason of a disposition of stock
received upon exercise of an ISO if the ISO Holding Period is satisfied.
Different rules apply if the optionee disposes of the shares of stock acquired
pursuant to the exercise of an ISO before the expiration of the ISO Holding
Period.
 
    RESTRICTED STOCK. A participant who is granted restricted stock may make an
election under Section 83(b) of the Code to have the grant taxed as compensation
income at the date of receipt, with the result that any future appreciation (or
depreciation) in the value of the shares of stock granted may be taxed as
capital gain (or loss) upon a subsequent sale of the shares. However, if the
participant does not make a Section 83(b) election, then the grant will be taxed
as compensation income at the full fair market value on the date that the
restrictions imposed on the shares expire. Unless a participant makes a Section
83(b) election, any dividends paid on stock subject to the restrictions are
compensation income to the participant and compensation expense to the Company.
The Company is generally entitled to an income tax deduction for any
compensation income taxed to the participant, subject to the provisions of
Section 162(m) of the Code.
 
    PERFORMANCE UNITS AND PERFORMANCE SHARES. A participant who has been granted
a performance unit or performance share award will not realize taxable income
until the applicable award cycle expires and the participant is in receipt of
the stock or cash distributed in payment of the award, at which time such
participant will realize ordinary income equal to the full fair market value of
the shares delivered or the amount of cash paid. At that time, the Company
generally will be allowed a corresponding tax deduction equal to the
compensation taxable to the award recipient, subject to the provisions of
Section 162(m) of the Code.
 
NEW PLAN BENEFITS
 
    It cannot be determined at this time what benefits or amounts, if any, will
be received by or allocated to any person or group of persons under the Amended
and Restated Equity Incentive Plan if the Amended and Restated Equity Incentive
Plan is adopted. This determination will be made by the Compensation Committee.
 
ACCOUNTING TREATMENT OF OPTIONS
 
    Under existing accounting rules, the Company incurs no compensation expense
upon the grant of a stock option with an exercise price at least equal to the
fair market value of Company Common Stock on the date of grant. However, in the
footnotes to the Company's annual financial statements, the Company sets forth
pro forma net income and earnings per share amounts which are calculated as if
the Company had elected to recognize compensation expense equal to the fair
value of the option on the grant date based on the Black-Scholes option pricing
model. The Financial Accounting Standards Board has proposed changes regarding
accounting for stock-based compensation which, if adopted, may alter the
accounting treatment of stock-based awards.
 
                                       13
<PAGE>
           ITEM 3--APPROVAL OF AMERICAN MEDICAL SECURITY GROUP, INC.
                        EXECUTIVE ANNUAL INCENTIVE PLAN
 
    The Executive Annual Incentive Plan (the "Annual Incentive Plan") will not
become effective with respect to individuals who are subject to Section 162(m)
of the Code unless the shareholder approval described below is obtained. The
purpose of the Annual Incentive Plan is to encourage superior performance by
executives of the Company and its subsidiaries through the payment of annual
cash incentive awards.
 
    The Annual Incentive Plan is designed to take into account Section 162(m) of
the Code, which generally denies corporate tax deductions for annual
compensation exceeding $1,000,000 paid to the chief executive officer and the
four other most highly compensated officers of a public company. Certain types
of compensation, including performance-based compensation, are excluded from
this deduction limit. In an effort to ensure that compensation payable under the
Annual Incentive Plan to certain executives will qualify as performance-based
compensation that is generally tax-deductible, the Annual Incentive Plan is
being submitted to shareholders of the Company. The Company believes
compensation payable pursuant to the Annual Incentive Plan will be deductible
for federal income tax purposes under most circumstances, but there can be no
assurance in this regard. Moreover, under certain circumstances such as death,
disability and retirement (all as defined in the Annual Incentive Plan),
compensation not qualified under Section 162(m) of the Code may be payable. By
approving the Annual Incentive Plan, the shareholders will be approving, among
other things, the performance measures, eligibility requirements and annual
incentive award limits contained therein.
 
    THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS A VOTE "FOR" APPROVAL OF THE
EXECUTIVE ANNUAL INCENTIVE PLAN.
 
    A copy of the Annual Incentive Plan is attached hereto as Appendix B. The
following description of certain provisions of the Annual Incentive Plan is
qualified in its entirety by reference to the complete text set forth in
Appendix B.
 
    ADMINISTRATION.  The Annual Incentive Plan will be administered by the
Compensation Committee. The Compensation Committee will have sole authority to
make rules and regulations relating to the administration of the Annual
Incentive Plan, and any interpretations and decisions of the Compensation
Committee with respect to the Annual Incentive Plan will be final and binding.
 
    ELIGIBILITY.  The Compensation Committee will, in its sole discretion,
determine those officers and salaried employees of the Company who shall be
eligible to participate in the Annual Incentive Plan for a given period of 12
months or less (a "Plan Year"). Participants will be selected by the
Compensation Committee based on its determination that such employee is or gives
promise of becoming of exceptional importance to the Company and of making
substantial contributions to the success, growth, and profit of the Company.
Participation in the Annual Incentive Plan by a participant during a given Plan
Year does not entitle continued participation by such participant in any
subsequent Plan year. The Compensation Committee does not anticipate identifying
any eligible employees or making any awards under the Annual Incentive Plan for
fiscal 1999. Accordingly, it is not possible to estimate at this time the number
of persons who will be eligible to participate in the Annual Incentive Plan.
 
    PLAN FEATURES.  The Annual Incentive Plan provides for the payment of cash
incentive awards to participants designated by the Compensation Committee, which
payments may be conditioned upon the attainment of such pre-established
performance goals as the Compensation Committee shall determine. Performance
goals may relate to one or more of the following business criteria, measured on
an absolute basis or in terms of growth or reduction: net income (pre-tax or
after-tax and with adjustments as stipulated), earnings per share, return on
equity, return on assets, return on tangible book value, operating income,
earnings before depreciation, interest, taxes and amortization (EBDITA), loss
ratio, expense ratio, increase in stock price, total shareholder return,
economic value added, and operating cash flow. With
 
                                       14
<PAGE>
respect to Participants who are not Covered Employees, the Committee may
establish other subjective or objective performance goals, including individual
goals, which it deems appropriate. Such performance goals may be different for
each participant.
 
    The chief executive officer of the Company shall recommend to the
Compensation Committee target award levels for eligible employees as soon as
practicable after each Plan year. The designation of award recipients and the
amount of such awards shall be determined by the Compensation Committee pursuant
to the applicable preestablished performance goals and other rules established
by the Compensation Committee. No award granted in any Plan Year to a
participant may exceed $3,000,000.
 
    AMENDMENT AND DISCONTINUANCE.  The Board will have the right to modify,
suspend, or terminate the Annual Incentive Plan at any time.
 
    NEW PLAN BENEFITS.  It cannot be determined at this time what benefits or
amounts, if any, will be received by or allocated to any person or group of
persons under the Annual Incentive Plan if the Annual Incentive Plan is adopted
or what benefits or amounts would have been received by or allocated to any
person or group of persons for the last fiscal year if the Annual Incentive Plan
had been in effect.
 
                                       15
<PAGE>
                             EXECUTIVE COMPENSATION
 
    The following table summarizes the total compensation paid by the Company to
the Chief Executive Officer, the four other most highly compensated executive
officers of the Company, the former Chief Executive Officer, and one other
former executive officer (the "Named Executive Officers") for services rendered
to the Company for the fiscal years ended December 31, 1998, 1997 and 1996.
 
                           SUMMARY COMPENSATION TABLE
<TABLE>
<CAPTION>
                                                                                             LONG-TERM COMPENSATION
                                                                                      ------------------------------------
                                                  ANNUAL COMPENSATION                       AWARDS ($)
                                    ------------------------------------------------  -----------------------    PAYOUTS
                                                                            OTHER                 SECURITIES   -----------
                                                                           ANNUAL     RESTRICTED  UNDERLYING      LTIP
        NAME AND PRINCIPAL                                                COMPENSA-     STOCK      OPTIONS/      PAYOUTS
             POSITION                 YEAR      SALARY($)   BONUS($)(1)  TION($)(2)     AWARDS    SARS(#)(3)     ($)(4)
- ----------------------------------  ---------  -----------  -----------  -----------  ----------  -----------  -----------
<S>                                 <C>        <C>          <C>          <C>          <C>         <C>          <C>
Samuel V. Miller..................       1998   $ 500,000    $ 650,000    $  14,200   $900,449(6)    201,113    $      --
  Chairman of the Board, President       1997     500,000      600,000           --           --          --           --
  & Chief Executive Officer              1996     500,004    1,500,000       89,169           --     673,043           --
Edward R. Skoldberg (7)...........       1998     225,000      110,000        2,741           --     129,531           --
  Executive Vice President & Chief       1997     199,716       90,000           --           --      23,232           --
  Operating Officer                      1996      15,977       50,000           --           --          --           --
Gary D. Guengerich (7)............       1998     225,000      110,000           --           --     152,788           --
  Executive Vice President, Chief        1997      37,262       85,000           --           --          --           --
  Financial Officer & Treasurer          1996          --           --           --           --          --           --
Timothy J. Moore (7)..............       1998     164,000       65,000           --           --      64,770           --
  Senior Vice President, General         1997     125,777       40,000           --           --      11,616           --
  Counsel & Secretary                    1996          --           --           --           --          --           --
Scott B. Westphal.................       1998     139,423       42,000           --           --      20,000           --
  Vice President & Chief Actuary         1997     125,962       31,250           --           --          --           --
                                         1996      92,500       13,406           --           --      19,727           --
Thomas R. Hefty (9)...............       1998     367,898           --        9,135           --      35,000       64,985
  Former Chairman of the Board,          1997     475,008       97,377        7,885           --      35,000        5,294
  President & Chief Executive            1996     410,028      177,542        9,355           --      30,000           --
  Officer
Roger A. Formisano (9)............       1998     185,697           --           --           --      35,000       35,165
  Former Executive Vice President        1997     244,536       22,008          904           --      25,000        2,894
  & Chief Operating Officer              1996     235,128       61,604        3,424           --      15,000           --
 
<CAPTION>
 
                                     ALL OTHER
        NAME AND PRINCIPAL           COMPENSA-
             POSITION               TION($)(5)
- ----------------------------------  -----------
<S>                                 <C>
Samuel V. Miller..................   $   2,000
  Chairman of the Board, President          --
  & Chief Executive Officer                 --
Edward R. Skoldberg (7)...........       3,750
  Executive Vice President & Chief          --
  Operating Officer                         --
Gary D. Guengerich (7)............          --
  Executive Vice President, Chief       50,000(8)
  Financial Officer & Treasurer             --
Timothy J. Moore (7)..............       2,117
  Senior Vice President, General            --
  Counsel & Secretary                       --
Scott B. Westphal.................       5,000
  Vice President & Chief Actuary            --
                                            --
Thomas R. Hefty (9)...............       4,000
  Former Chairman of the Board,          4,000
  President & Chief Executive            3,750
  Officer
Roger A. Formisano (9)............       4,000
  Former Executive Vice President        4,000
  & Chief Operating Officer              3,750
</TABLE>
 
- ------------------------
 
(1) Bonus amounts for Mr. Miller represent amounts earned by him pursuant to the
    terms of his employment agreement with the Company. Bonus amounts for other
    executive officers represent amounts earned under incentive bonus plans, and
    for Messrs. Guengerich and Skoldberg include signing bonuses for joining the
    Company.
 
(2) Amounts represent reimbursement for the payment of taxes and, for former
    executive officers, the payout for unused personal days. The amounts
    indicated do not include perquisites and other personal benefits to the
    Named Executive Officers which, for each officer, did not exceed the lesser
    of $50,000 or 10% of the officer's total annual salary and bonus.
 
(3) Numbers reflect adjustments made in 1998, as a result of the Spin-off, to
    the number of stock options granted prior to the Spin-off. The numbers for
    Mr. Formisano include an aggregate of 75,000 stock options that were
    converted to stock options of United Wisconsin Services in 1998 as a result
    of the Spin-Off.
 
(4) The 1996-1998 Long-Term Incentive Plan and the 1997-1999 Long-Term Incentive
    Plan were discontinued during 1998 and pro rata payouts were made to Messrs.
    Hefty and Formisano in the amounts of $59,691 and $32,270, respectively.
 
                                       16
<PAGE>
(5) Amounts represent the Company's matching contributions to the Company's
    retirement savings plan and, for former officers, contributions to the
    UWSI/BCBSUW 401(k) Plan.
 
(6) Consists of a grant of 73,506 shares of deferred stock pursuant to an
    agreement entered into with Mr. Miller on November 17, 1998. The deferred
    stock will vest on November 17, 2002, or his earlier death, disability, the
    occurrence of a change in control while he is employed by the Company, or
    upon the Company's termination of his employment for any reason other than
    cause if the fair market value of the Common Stock on the date of
    termination exceeds $12.00. If the vesting requirements are satisfied, the
    deferred stock will be issued on January 2 of the year following Mr.
    Miller's termination of employment. Mr. Miller has the right to receive
    stock dividends, if any, on the deferred stock. As of December 31, 1998, the
    73,506 shares of deferred stock had a value of $1,052,055 based on the
    $14.3125 closing price of the Company's Common Stock on December 31, 1998.
 
(7) Messrs. Skoldberg, Guengerich, and Moore became employees of the Company on
    November 18, 1996, November 3, 1997, and March 3, 1997, respectively.
 
(8) The amount represents payment in lieu of commission reimbursement upon sale
    of home, which Mr. Guengerich chose not to sell.
 
(9) As a result of the Spin-off, Messrs. Hefty and Formisano ceased to be
    officers of the Company on September 25, 1998.
 
                                       17
<PAGE>
    The following table details the stock options granted pursuant to the
Company's Equity Incentive Plan during 1998 to the Named Executive Officers. No
SARs were granted during 1998.
 
                   OPTION/SAR GRANTS IN LAST FISCAL YEAR (1)
 
<TABLE>
<CAPTION>
                                                                                                      POTENTIAL REALIZED VALUE
                                                              INDIVIDUAL GRANTS                              AT ASSUMED
                                          ----------------------------------------------------------   ANNUAL RATES OF STOCK
                                            NUMBER OF    PERCENT OF TOTAL                                      PRICE
                                           SECURITIES       OPTION/SARS                               APPRECIATION FOR OPTION
                                           UNDERLYING       GRANTED TO      EXERCISE OR                         TERM
                                          OPTIONS/SARS     EMPLOYEES IN     BASE PRICE   EXPIRATION   ------------------------
NAME                                       GRANTED (#)      FISCAL YEAR      ($/SHARE)      DATE        5% ($)      10% ($)
- ----------------------------------------  -------------  -----------------  -----------  -----------  ----------  ------------
<S>                                       <C>            <C>                <C>          <C>          <C>         <C>
 
Samuel V. Miller........................      100,000             11.9%      $   10.25      9/27/10   $  815,750  $  2,191,890
                                              101,113             12.0           12.25     11/16/10      985,771     2,648,726
 
Edward R. Skoldberg.....................       70,000              8.3           10.25      9/27/10      571,025     1,534,323
                                               50,000              5.9           12.00      9/27/10      320,375     1,008,445
                                                9,531              1.1           12.25     11/16/10       92,920       249,671
 
Gary D. Guengerich......................       23,232              2.8           17.43      2/18/10      322,270       865,922
                                               70,000              8.3           10.25      9/27/10      571,025     1,534,323
                                               50,000              5.9           12.00      9/27/10      320,375     1,008,445
                                                9,556              1.1           12.25     11/16/10       93,163       250,326
 
Timothy J. Moore........................       35,000              4.2           10.25      9/27/10      285,513       767,162
                                               25,000              3.0           12.00      9/27/10      160,188       504,223
                                                4,770               .6           12.25     11/16/10       46,504       124,953
 
Scott B. Westphal.......................       20,000              2.4           10.25      9/27/10      163,150       438,378
 
Thomas R. Hefty.........................       35,000              4.2           16.13       1/1/10      449,302     1,207,248
 
Roger A. Formisano(2)...................       35,000              4.2             N/A          N/A          N/A           N/A
</TABLE>
 
- ------------------------
 
(1) The grants consisted entirely of nonqualified stock options granted pursuant
    to the Equity Incentive Plan. All options granted have a term of 12 years.
    The options granted at $12.00 per share to Messrs. Skoldberg, Guengerich and
    Moore were granted at a premium of $1.75 per share over the fair market
    value of the Company's Common Stock on the date of grant. All other options
    granted to the Named Executive Officers were granted at 100% of the fair
    market value of the Company's Common Stock on the date of grant. The options
    that expire on September 27, 2010 vest and become exercisable as to 25% of
    such options on each of the first four anniversaries of the date of grant.
    All other options granted to the Named Executive Officers are 100% vested
    and exercisable. Exercisability of unvested options is accelerated in the
    event of a named Executive Officer's death, disability, or upon a change in
    control. A change in control includes: the acquisition by certain persons or
    groups of 25% or more of the outstanding Common Stock; a change in the
    membership of a majority of the Board of Directors during any two year
    period in certain circumstances; or the approval by the Company's
    shareholders of a plan of liquidation, an agreement to sell substantially
    all of the Company's assets, or certain mergers, consolidations or
    reorganizations. Notwithstanding the foregoing, no option may be exercised
    within the first six months following the date of grant.
 
(2) In connection with the Spin-off, the options granted to Mr. Formisano were
    canceled and converted into options to purchase shares of United Wisconsin
    Services.
 
                                       18
<PAGE>
    No stock options or SARs were exercised by any of the Named Executive
Officers during 1998. The number of unexercised options and the total value of
unexercised in-the-money options at December 31, 1998, are shown in the
following table. No SARs were outstanding at December 31, 1998.
 
              AGGREGATED OPTION/SAR EXERCISES IN LAST FISCAL YEAR
                     AND FISCAL YEAR END OPTION/SAR VALUES
 
<TABLE>
<CAPTION>
                                                            NUMBER OF SECURITIES         VALUE OF UNEXERCISED
                                                           UNDERLYING UNEXERCISED      IN-THE-MONEY OPTIONS/SARS
                                                         OPTIONS/SARS AT FY-END(#)         AT FY-END ($)(1)
                                                        ----------------------------  ---------------------------
NAME                                                     EXERCISABLE   UNEXERCISABLE  EXERCISABLE   UNEXERCISABLE
- ------------------------------------------------------  -------------  -------------  ------------  -------------
<S>                                                     <C>            <C>            <C>           <C>
 
Samuel V. Miller......................................      972,175         100,000   $  1,320,347   $   406,250
 
Edward R. Skoldberg...................................       32,763         120,000         19,658       400,000
 
Gary D. Guengerich....................................       32,788         120,000         19,709       400,000
 
Timothy J. Moore......................................       16,386          60,000          9,838       200,000
 
Scott B. Westphal.....................................       19,727          20,000        222,964        81,250
 
Thomas R. Hefty.......................................      155,543              --             --            --
 
Roger A. Formisano....................................           --              --             --            --
</TABLE>
 
- ------------------------
 
(1) The value of unexercised in-the-money options represents the positive spread
    between the $14.3125 per share closing price of the Company's Common Stock
    as reported on the New York Stock Exchange composite tape on December 31,
    1998, and the exercise price of unexercised options. The actual amount, if
    any, realized upon exercise of options will depend on the market price of
    the Common Stock relative to the per share exercise price at the time the
    option is exercised. There is no assurance that the values of unexercised
    in-the-money options reflected in this table will be realized.
 
EMPLOYMENT AND RELATED AGREEMENTS
 
    Mr. Miller is a party to an Employment and Noncompetition Agreement (the
"Miller Agreement") with the Company dated as of April 7, 1998, which supersedes
an Employment and Noncompetition Agreement dated as of October 30, 1995. The
Miller Agreement contains customary employment terms. The terms of the Miller
Agreement, which expires on December 31, 2000, provide for automatic one-year
extensions (unless notice not to extend is given by either party at least 30
days prior to the end of the effective term), and provide for an annual base
salary of $500,000 and annual performance bonuses of not less than $500,000 or
more than $1,000,000. Portions of Mr. Miller's performance bonuses are deferred
so that his W-2 compensation for a calendar year does not exceed $990,000. In
the event of termination of the employment of Mr. Miller by the Company without
"cause" (as defined in the Miller Agreement), Mr. Miller will be entitled to
receive a severance payment of $1,000,000 if his employment is terminated during
a renewal term of the Miller Agreement, provided that such severance amount
shall not exceed 2.99 multiplied by Mr. Miller's "base amount" (as defined in
Internal Revenue Code Section 280G). The Miller Agreement also includes
noncompetition and confidentiality provisions.
 
    The Company has also entered into an Employment Agreement with Mr. Westphal
dated as of August 21, 1996 (the "Westphal Agreement"), which contains customary
employment terms, continues until terminated by either party, and provides for
an annual base salary of an amount to be adjusted annually and participation in
the Company's incentive bonus arrangements. In the event of termination of the
employment of Mr. Westphal by the Company without cause, Mr. Westphal shall be
entitled to receive an amount equal to one-year's base salary. The Westphal
Agreement also includes provisions relating to confidentiality and
nonsolicitation of employees or customers.
 
                                       19
<PAGE>
    Messrs. Skoldberg, Guengerich, Moore and Westphal participate in the
American Medical Security Group, Inc. Change of Control Severance Benefit Plan
(the "Severance Plan"). Benefits are payable under the Severance Plan if, during
a period beginning six months prior to a "change of control" and ending on the
second anniversary of a change of control, (i) the participant's employment is
terminated by the Company, except for "cause," as defined in the Severance Plan,
death or disability, or (ii) the participant voluntarily terminates employment
with "good reason," as defined in the Severance Plan. For purposes of the
Severance Plan, a "change of control" shall have occurred when (i) a majority of
the directors of the Company cease to continue to serve as directors of the
Company and/or the chief executive officer of the Company ceases to serve as the
chief executive of the Company as the result of (a) any person, or group as
defined in Section 13(d)(3) of the Exchange Act, becoming the beneficial owner
of 40% of the Company's outstanding voting securities, (b) a cash tender or
exchange offer, (c) a merger or other business combination, (d) a sale of
substantially all of the assets of the Company, (e) a contested election of
directors, or (f) any combination of the foregoing events; or (ii) the
shareholders approve a plan of liquidation or dissolution of the Company. Plan
benefits include the payment of severance equal to three times the average
salary and bonus for the prior two years for Executive and Senior Vice
Presidents and one and one-half times the average salary and bonus for the prior
two years for participants who are not Executive or Senior Vice Presidents. In
addition, the Company would also provide health, dental, long-term disability
and life insurance coverage for comparable periods of time.
 
    In connection with the employment offers accepted by Messrs. Skoldberg,
Guengerich and Moore, the Company has also agreed to provide Messrs. Skoldberg,
Guengerich and Moore with severance benefits in the event of termination of
their employment by the Company without cause. These benefits include payments
equal to one year's salary and medical insurance coverage for one year.
 
            COMPENSATION COMMITTEE REPORT ON EXECUTIVE COMPENSATION
 
INTRODUCTION
 
    The Compensation Committee of the Board of Directors (the "Compensation
Committee") is comprised of four independent, non-employee directors. The
Compensation Committee establishes and directs the administration of all
programs under which executive compensation is paid or awarded to the Company's
executive officers. In addition, the Compensation Committee evaluates executive
officer performance and assesses the overall effectiveness of the Company's
executive compensation programs.
 
COMPENSATION PHILOSOPHY AND OBJECTIVES
 
    The Company's compensation and benefit programs are designed:
 
    - To attract and retain top level executive talent required to attain the
      Company's short and long-term goals.
 
    - To motivate these executives to achieve the goals of the Company's
      business strategy.
 
    - To link executive and shareholder financial interests through appropriate
      equity-based long-term incentive plans.
 
    - To provide a compensation package that recognizes individual contributions
      and overall business results.
 
BUSINESS CONSIDERATIONS
 
    During fiscal 1998, the Company transferred its managed care and specialty
products business to its wholly owned subsidiary, Newco/UWS, Inc. ("Newco/UWS"),
and distributed shares of common stock of Newco/UWS to the Company's
shareholders (the "Spin-off"). In connection with the Spin-off, the Company
changed its name from United Wisconsin Services, Inc. to American Medical
Security
 
                                       20
<PAGE>
Group, Inc., and Newco/UWS was renamed United Wisconsin Services, Inc. The
Company continues to own the small group business. See "Certain Transactions."
 
    As a result of the Spin-off, substantial changes in the management of the
Company occurred. The senior management of American Medical Security Holdings,
Inc. ("AMS Holdings") became the management of the Company. Following the
Spin-off, the Company's Board of Directors consisted of three continuing
directors, two of whom were also directors of AMS Holdings, and six new
directors, five of whom were also directors of AMS Holdings. Four new members
were elected to the Compensation Committee to replace directors who left office
or ceased to be members of the Compensation Committee.
 
    As a result of the Spin-off, the Compensation Committee is in the process of
evaluating the current executive compensation program in relation to its
philosophy and objectives. In connection with the Spin-off, several compensation
issues arose as to the new executives of the Company that are discussed in this
report.
 
ELEMENTS OF EXECUTIVE COMPENSATION
 
    The elements of executive compensation include base salary, an annual
incentive program, and an equity incentive plan. The Compensation Committee's
decisions with respect to each of these elements are discussed below. While the
elements of compensation described in this report are considered separately, the
Compensation Committee takes into account the full compensation package afforded
by the Company to the individual, including salary, incentive compensation,
retirement, and other benefits. In reviewing the individual performance of the
executives whose compensation is detailed in this proxy statement, other than
the Chief Executive Officer (CEO), the Compensation Committee takes into account
the views of Mr. Miller, the CEO.
 
    Each year the Compensation Committee reviews the Company's executive
compensation program to ensure that pay opportunities are competitive with the
current market and that there is appropriate linkage between Company performance
and executive compensation. This process includes consultation with a national
compensation and benefits consultant on issues of base salary, annual incentive
awards, stock options and other long-term equity awards, and overall
compensation. The Compensation Committee's review includes comparison of the
Company's executive compensation against an appropriate peer group. During 1998,
the peer group included a composite of comparably sized health and life
insurance companies as surveyed by Hewitt Associates LLC. Certain of the
companies in the peer group are included in the peer index included in the
Performance Graph contained in this proxy statement.
 
BASE SALARY
 
    Base salaries are set in a context of total direct pay (base salary plus
targeted annual incentive) such that total direct pay is competitive with
current market levels of the comparable group and that there is appropriate
linkage between Company performance and executive compensation. Base salaries
for executive officers are initially determined by evaluating and comparing the
responsibilities of their positions and experiences and by reference to the
competitive marketplace for executive talent. After the Spin-off, the Committee
affirmed the 1998 compensation currently in place for the executive officers.
 
ANNUAL INCENTIVE COMPENSATION
 
    Except for the CEO, the Company's executive officers are eligible for an
annual performance bonus under the Company's incentive program (the "Annual
Program"). The bonus paid under the Annual Program has two components: (i)
assessment of specific job performance characteristics and (ii) achievement of
assigned and expected performance objectives.
 
    The Annual Program is designed to reward those executives who made
significant contributions to the Company's business objectives. Participants in
the Annual Program are high performers around whom the
 
                                       21
<PAGE>
new Company's high performance work culture will be built. The Annual Program
focuses on pre-planned business and personal objectives. Not all individual
performance objectives are quantifiable and thus the Compensation Committee did
not assign weights to different factors or follow mathematical formulae.
Therefore, the Compensation Committee used discretion in evaluating the
executives' achievements of their individual performance objectives.
 
    For 1998, the potential range of bonus awards was 0% to 70% of annual
compensation with the actual payout ranging from 25% to 49%. The awards for
fiscal 1998 were paid in the first quarter of 1999.
 
LONG-TERM INCENTIVE COMPENSATION
 
    Long-term incentives are provided primarily pursuant to the Company's Equity
Incentive Plan, as amended and restated September 25, 1998 (the "Equity
Incentive Plan"), which provides for the grant of stock options, stock
appreciation rights, restricted stock, and performance unit and performance
shares.
 
    The purpose of the Equity Incentive Plan is to promote the success, and
enhance the value of the Company by linking the personal interests of employees
to those of the Company shareholders, and by further providing employees that
receive an award under the Equity Incentive Plan with an incentive for
outstanding performance. When awarding long-term incentives, the Compensation
Committee considers executives' levels of responsibility, prior experience,
historical award data, and compensation practice at comparative companies.
 
    The Compensation Committee is responsible for administering the Equity
Incentive Plan. Currently only nonqualified stock option grants are outstanding
under the Equity Incentive Plan. The option grants are designed to motivate
employees to maximize shareholder value and maintain a medium to long-term
perspective. Option grants are made at no less than the fair market price on the
date of grant and generally become exercisable in equal annual installments over
a four-year term, generally expiring no later than 12 years after the date of
grant. All full-time active employees of the Company are eligible to participate
in the Equity Incentive Plan.
 
    When determining the size of the option grants made to executives in 1998,
the Compensation Committee considered the results of a survey performed by
Hewitt Associates LLC on equity authorization for companies undergoing
restructurings comparable to the Spin-off. The Compensation Committee also
considered its own evaluation of the executives' past and prospective
contributions to the success of the Company, anticipated performance
requirements and contributions of each executive officer, and historical option
award data. In connection with the Spin-off, the Compensation Committee made a
special one-time incentive grant designed to enhance links between the fortunes
of the Company's shareholders and key executives.
 
    In addition, certain unexpected results were created as a result of the
option adjustment formulae used in connection with the Spin-off. In order to
resolve this matter, the Compensation Committee awarded additional option grants
to senior executives and a deferred stock grant (described below) to the
Company's CEO to achieve comparable levels of value intended to be awarded.
 
    Nonqualified stock options to purchase a total of 367,089 shares were
granted to the Company's current executive officers (other than the CEO) named
in the compensation table for fiscal 1998. Certain of the option grants to
executive officers were made at a premium price of $12.00 per share. The awards
to the CEO are discussed below.
 
CHIEF EXECUTIVE OFFICER COMPENSATION
 
    During 1998, Mr. Miller became the CEO of the Company. Mr. Miller's
employment and noncompetition agreement with the Company was renewed effective
as of April 7, 1998, with a term ending on December 31, 2000 (the "Miller
Agreement"). Under the terms of the Miller Agreement, Mr. Miller's
 
                                       22
<PAGE>
annual base salary is $500,000 and he is eligible for an annual performance
bonus of not less than $500,000 or more than $1 million.
 
    In determining the individual performance portion of Mr. Miller's annual
incentive award, the Compensation Committee considered the financial performance
and growth of the Company, as well as Mr. Miller's leadership and implementation
of the Spin-off and overall strategic direction of the Company. Mr. Miller
received an annual incentive award of $650,000 or 130% of base salary.
 
    In 1998, Mr. Miller received options to purchase 100,000 shares at an
exercise price of $10.25 per share and 101,113 shares at $12.25 per share as
detailed in the option grant table contained in this proxy statement. This
equity interest recognizes Mr. Miller's leadership in the turnaround of the
small group business and completion of the Spin-off, and provides an appropriate
link to the interests of shareholders.
 
    Pursuant to a deferred stock agreement dated November 17, 1998, Mr. Miller
received a grant of 73,506 shares that will vest on November 17, 2002, or
earlier upon Mr. Miller's death, disability or a change in control while he is
employed by the Company, or upon the Company's termination of his employment for
any reason other than cause if the fair market value of the Company's Common
Stock on the date of termination exceeds $12.00. Once vested, the shares will be
distributed to Mr. Miller on January 2 of the year following the calendar year
during which Mr. Miller's employment with the Company terminates.
 
    Mr. Miller also participates in a deferral program whereby a portion of his
annual performance bonus is deferred until he is no longer an employee of the
Company or he is no longer considered a "covered employee" within the meaning of
Section 162(m)(3) of the Code. The deferred amounts are held in a rabbi trust
and are credited at an interest rate equal to 60% of the prime rate as reported
in the Wall Street Journal.
 
POLICY ON DEDUCTIBILITY OF COMPENSATION
 
    Section 162(m) of the Internal Revenue Code of 1986, as amended, limits the
Company's federal income tax deduction for compensation to its CEO and any of
its four other highest paid executive officers to $1 million. Qualified
performance-based compensation is not subject to the $1 million limitation,
provided certain requirements of Section 162(m) are satisfied. In 1998, none of
the Company's executives received compensation in excess of $1 million for
purposes of Section 162(m) and all executive compensation paid in fiscal 1998 is
fully deductible. In order to preserve the deductibility of Mr. Miller's
compensation, a portion of his annual incentive for 1998 was deferred pursuant
to the deferral program described above. The Compensation Committee has,
however, reviewed Section 162(m) and considered its impact on the Company's
future executive compensation plans.
 
CONCLUSION
 
    After its review of the total compensation program for the executives of the
Company, the Compensation Committee continues to believe that these executive
compensation policies and practices serve the interests of the shareholders and
the Company effectively. We also believe that the various compensation programs
offered are appropriately balanced to provide increased motivation for executive
officers to contribute to the Company's overall future successes, thereby
increasing the value of the Company for the shareholders' benefit. The
Compensation Committee will continue to monitor the effectiveness of the
Company's total compensation program to meet the ongoing needs of the Company.
 
                                          COMPENSATION COMMITTEE
                                          Michael T. Riordan, Chairman
                                          Roger H. Ballou
                                          W. Francis Brennan
                                          Frank L. Skillern
 
                                       23
<PAGE>
                               PERFORMANCE GRAPH
 
    Two performance graphs are presented below to provide cumulative shareholder
return information for the Company on (i) a post-Spin-off basis reflecting
continuing operations and (ii) a five-year historical basis, as is require by
Exchange Act reporting regulations. The first graph compares the cumulative
shareholder return of the Company's Common Stock for the period from September
28, 1998, (the first day of trading, following the completion of the Spin-off,
under American Medical Security Group Inc.'s original listing on the New York
Stock Exchange) to December 31, 1998, to the cumulative total returns of the
NYSE/AMEX/Nasdaq Stock Market and the Morgan Stanley Healthcare Payor Index. The
second performance graph compares the cumulative shareholder return of the
Company's Common Stock (traded on the New York Stock Exchange prior to the
Spin-off under the listing of United Wisconsin Services and after the Spin-off
under the listing of American Medical Security Group, Inc.) to the cumulative
total returns of the NYSE/AMEX/Nasdaq Stock Market and the Morgan Stanley
Healthcare Payor Index for the five year period ended December 31, 1998. The
graphs assume an investment of $100 in each of the Company's Common Stock, the
NYSE/AMEX/Nasdaq Stock Market, and the Morgan Stanley Healthcare Payor Index at
the beginning of the periods (September 28, 1998, and December 31, 1993, as the
case may be), and assume reinvestment of dividends. In the five-year graph, the
Spin-off of the Company's managed care and specialty products business was
treated as a special dividend of $7.19 per share that was reinvested in Company
Common Stock on September 28, 1998, the first day of trading following the Spin-
off. The line graphs are not intended to be indicative of future stock
performance.
 
                     COMPARISON OF CUMULATIVE TOTAL RETURNS
               FROM SEPTEMBER 28, 1998 THROUGH DECEMBER 31, 1998
                               PERFORMANCE GRAPH
                     AMERICAN MEDICAL SECURITY GROUP, INC.
 
EDGAR REPRESENTATION OF DATA POINTS USED IN PRINTED GRAPHIC
 
<TABLE>
<CAPTION>
           AMERICAN MEDICAL     NYSE/AMEX/NASDAQ    MORGAN STANLEY
 
<S>        <C>                <C>                   <C>
                    Security          Stock Market      Health Care
                 Group, Inc.        (US Companies)      Payor Index
09/28/98             $100.00               $100.00          $100.00
10/02/98              $92.68                $95.55           $91.92
10/09/98              $63.42                $92.41           $88.18
10/16/98              $71.95                $99.41           $96.78
10/23/98              $73.17               $101.44           $99.15
10/30/98              $85.37               $104.46          $113.22
11/06/98             $112.20               $108.85          $118.10
11/13/98             $111.59               $107.37          $112.20
11/20/98             $117.07               $110.70          $116.17
11/27/98             $137.81               $113.48          $116.36
12/04/98             $140.24               $112.11          $116.32
12/11/98             $137.20               $110.98          $116.67
12/18/98             $140.24               $112.80          $114.03
12/24/98             $142.68               $116.42          $113.14
12/31/98             $139.63               $117.94          $118.36
</TABLE>
 
<TABLE>
<CAPTION>
                                                                            9/28/98   10/30/98   11/27/98   12/31/98
                                                                           ---------  ---------  ---------  ---------
<S>                                                                        <C>        <C>        <C>        <C>
American Medical Security Group, Inc.....................................  $  100.00  $   85.37  $  137.81  $  139.63
Morgan Stanley Health Care Payor Index...................................     100.00  $  113.22  $  116.36     118.36
NYSE/AMEX/Nasdaq Stock Market (US Companies).............................     100.00  $  104.46  $  113.48     117.94
</TABLE>
 
                                       24
<PAGE>
                     COMPARISON OF CUMULATIVE TOTAL RETURNS
                FROM DECEMBER 31, 1993 THROUGH DECEMBER 31, 1998
                               PERFORMANCE GRAPH
                     AMERICAN MEDICAL SECURITY GROUP, INC.
 
EDGAR REPRESENTATION OF DATA POINTS USED IN PRINTED GRAPHIC
 
<TABLE>
<CAPTION>
           AMERICAN MEDICAL     NYSE/AMEX/NASDAQ    MORGAN STANLEY
 
<S>        <C>                <C>                   <C>
                    Security          Stock Market      Health Care
                 Group, Inc.        (US Companies)      Payor Index
12/31/93             $100.00               $100.00          $100.00
12/31/94             $121.32                $99.50          $131.03
12/31/95              $75.83               $135.67          $164.46
12/31/96              $92.34               $164.47          $143.42
12/31/97              $92.05               $215.32          $149.10
12/31/98              $88.37               $265.86          $159.07
</TABLE>
 
<TABLE>
<CAPTION>
                                                       12/31/93   12/31/94   12/31/95   12/31/96   12/31/97   12/31/98
                                                       ---------  ---------  ---------  ---------  ---------  ---------
<S>                                                    <C>        <C>        <C>        <C>        <C>        <C>
American Medical Security Group, Inc.................  $  100.00  $  121.32  $   75.83  $   92.34      92.05      88.37
Morgan Stanley Health Care Payor Index...............     100.00     131.03     164.46     143.42     149.10     159.07
NYSE/AMEX/Nasdaq Stock Market (US Companies).........     100.00      99.50     135.67     164.47     215.32     265.86
</TABLE>
 
                                       25
<PAGE>
                              CERTAIN TRANSACTIONS
 
    On May 27, 1998, the Board of Directors of the Company, then known as United
Wisconsin Services, Inc., approved a plan to spin off its managed care companies
and specialty products business to its shareholders. On September 11, 1998, the
Company contributed all of its subsidiaries comprising the managed care and
specialty products business to a newly created subsidiary named "Newco/UWS,
Inc.", a Wisconsin corporation ("Newco/UWS"). On September 25, 1998, the Company
spun off the managed care and specialty products business through a distribution
of 100% of the issued and outstanding shares of common stock of Newco/UWS to the
Company's shareholders of record as of September 11, 1998 (the "Spin-off"). In
connection with the Spin-off, the Company adopted its current name of American
Medical Security Group, Inc. and Newco/UWS changed its name to United Wisconsin
Services, Inc. (referred to herein as "United Wisconsin Services"). As a result
of the transactions entered into in connection with the Spin-off, United
Wisconsin Services owns the businesses and assets of, and is responsible for the
liabilities associated with, the managed care and specialty products business
formerly conducted by the Company. The Company continues to own the business and
assets of, and is responsible for the liabilities associated with, the Company's
small group business described in the Company's Annual Report on Form 10-K for
the fiscal year ended December 31, 1998.
 
SERVICE AGREEMENTS
 
    Blue Cross, a 37.9% beneficial shareholder of the Company, beneficially owns
more than 10% of the common stock of United Wisconsin Services. The Company and
United Wisconsin Services are parties to a service agreement (the "UWS Service
Agreement") dated September 25, 1998, pursuant to which United Wisconsin
Services provides investment management and investment accounting services to
the Company. Fees under the UWS Service Agreement are based on a percentage of
the portfolio plus a flat rate for each corporate entity whose investments are
being managed by United Wisconsin Services. For fiscal 1998, the Company paid
United Wisconsin Services $48,407 for such services. The UWS Service Agreement
will terminate on December 31, 1999, unless terminated earlier upon appropriate
notice.
 
    Prior to the Spin-off, the Company and Blue Cross were parties to service
agreements (the "Service Agreements") with respect to the reciprocal provision
of certain services, including sales and marketing, rental of office space,
computerized data processing, claims processing, and legal, investment,
actuarial and other management services, related to the operation of the
Company's managed care and specialty products business. Pursuant to the Service
Agreements, the Company received net payments of $5.8 million, $5.3 million and
$4.0 million from Blue Cross for the years ended December 31, 1996, 1997 and
1998, respectively. The Service Agreements were assigned to United Wisconsin
Services effective September 11, 1998.
 
    Blue Cross and Electronic Data Systems Corporation are parties to a service
agreement (the "EDS Servicing Agreement") whereby EDS developed integrated
processing systems, maintained computer hardware and software and provided data
processing personnel for key systems (including claims, membership actuarial,
commission, general ledger, accounts payable and fixed assets) related to the
Company's managed care and specialty products business which was transferred to
United Wisconsin Services in connection with the Spin-off. The Company paid
approximately $3.5 million, $3.7 million and $2.4 million for the years ended
December 31, 1996, 1997 and 1998, respectively, for services pursuant to the EDS
Servicing Agreement. As of September 11, 1998, the Company no longer received
services under the EDS Servicing Agreement.
 
REINSURANCE AGREEMENTS
 
    During 1998, the Company and United Wisconsin Services, or their
subsidiaries, entered into various quota share reinsurance agreements
("Reinsurance Agreements") pursuant to which each company cedes
 
                                       26
<PAGE>
to the other certain risks related to life insurance, health insurance, dental
insurance, point-of-service and other insurance plans. In addition, each company
acting as the reinsurer provides administrative services to the other company
acting as the ceding company. As consideration for such reinsurance, the ceding
company receives a ceding commission of approximately 0.5% of the gross premiums
reinsured under each applicable agreement. For fiscal 1998, the Company received
$24,100 from United Wisconsin Services or its subsidiaries and paid $42,590 to
United Wisconsin Services or its subsidiaries pursuant to the Reinsurance
Agreements.
 
HEALTH AND OTHER BENEFITS TO THE EMPLOYEES OF BLUE CROSS
 
    Prior to the Spin-off, certain subsidiaries of the Company provided health,
life and other insurance benefits to the employees of Blue Cross. Premium
revenue received from Blue Cross for these services totaled $4.4 million, $4.5
million and $3.1 million in 1996, 1997 and 1998, respectively. In addition, Blue
Cross provided health insurance to certain of the Company's employees prior to
the Spin-off.
 
REGISTRATION RIGHTS AGREEMENTS
 
    The Company and Blue Cross have entered into a Registration Rights Agreement
dated as of September 1, 1998, which contains certain registration rights
granted by the Company with respect to shares owned by Blue Cross. Pursuant to
the terms of the agreement, Blue Cross is entitled to certain demand
registration rights until the earlier of July 31, 2008, or the date on which
Blue Cross owns in the aggregate less than three percent of the Company's
outstanding Common Stock. In addition, Blue Cross is entitled, subject to
certain limitations, to register shares of Common Stock in connection with a
registration statement prepared by the Company to register its equity
securities. Also, if Blue Cross proposes to sell its Common Stock to a third
party, Blue Cross may request that the Company register its shares prior to such
sale, and the Company shall use its best efforts to register all of the shares
that Blue Cross proposes to sell. Blue Cross has agreed not to acquire any
additional Common Stock of the Company, other than as a result of any stock
dividend or distribution, without the consent of the Company, for a period of
ten years.
 
    Wallace J. Hilliard, a 5.4% beneficial shareholders of the Company, and
Ronald A. Weyers, a former greater than 5% shareholder of the Company,
(together, the "Holders") have entered into a Registration Rights and Stock
Restriction Agreement with the Company dated as of December 3, 1996, which
contains certain registration rights granted by the Company with respect to
shares owned by the Holders. Pursuant to the terms of the agreement, the Holders
are entitled to certain demand registration rights until the earlier of December
3, 2001, or the date on which the Holders own in the aggregate less than three
percent of the Company's outstanding Common Stock. In addition, the Holders are
entitled, subject to certain limitations, to register shares of Common Stock in
connection with a registration statement prepared by the Company to register its
equity securities. The Holders have also agreed not to acquire any securities of
the Company without the consent of the Company for a period of ten years if such
acquisition would require regulatory approval, application or notification other
than as required by the Exchange Act. Further, the Holders have agreed not to
(i) initiate any shareholder proposals with respect to the Company, (ii) make
any proposals with respect to a merger or other business combination, sale or
transfer of assets, liquidation or other extraordinary corporate transaction of
the Company, or (iii) participate in a group (within the meaning of Section
13(d)(3) of the Exchange Act) with respect to the Company's securities or seek
to exercise control over the Company.
 
SETTLEMENT AGREEMENT
 
    In April 1998, the Company, Newco/UWS, Wallace J. Hilliard and Ronald A.
Weyers entered into a Settlement Agreement (the "Settlement Agreement") related
to matters arising out of the Company's acquisition of American Medical Security
Group, Inc., a Delaware corporation, ("Old AMSG") in December 1996. Under the
terms of the acquisition agreement, $8.0 million of the purchase price was
 
                                       27
<PAGE>
deposited into an escrow account as security for indemnification payments to be
made to the Company for breaches of certain representations, warranties,
covenants and other agreements contained in the acquisition agreement. In the
Settlement Agreement, the parties agreed to settle all claims against the escrow
for $500,000 and release the remaining escrow amount to the shareholders of Old
AMSG. The Company received the $500,000 settlement payment in fiscal 1998.
 
OTHER AGREEMENTS
 
    Mr. Hilliard and Mr. Weyers are parties to Employment and Noncompetition
Agreements with the Company entered into as of December 3, 1996, and amended
March 30, 1999, pursuant to which Mr. Hilliard and Mr. Weyers continue to
received payments. The agreements provide for the payment of (i) $750,000 per
year during the first year, (ii) $500,000 per year for the next four years and
three months for Mr. Hilliard and $500,000 per year for the next four years for
Mr. Weyers, and (iii) $100,000 per year thereafter for a period of three years.
The agreements contain noncompetition and nonsolicitation provisions applicable
during the term of the agreements and for a period of two years thereafter. Mr.
Hilliard's and Mr. Weyers' agreements expire on March 3, 2005, and December 2,
2004, respectively. On March 30, 1999, Mr. Hilliard and Mr. Weyers entered into
Option Surrender Agreements with the Company pursuant to which they surrendered
stock options to purchase 530,000 and 470,000 shares of Company Common Stock,
respectively. As a result, Mr. Hilliard ceased to be a greater than 5%
beneficial shareholder of the Company. Mr. Weyers ceased to be a greater than 5%
beneficial shareholder of the Company in 1998.
 
            SECTION 16(A) BENEFICIAL OWNERSHIP REPORTING COMPLIANCE
 
    Section 16(a) of the Exchange Act requires the Company's executive officers
and directors and any persons who beneficially own in excess of ten percent of
the shares of the Common Stock outstanding to file reports of ownership and
changes in ownership of the Common Stock with the Securities and Exchange
Commission, the New York Stock Exchange and the Company.
 
    Based upon a review of the information furnished to the Company, the Company
believes that during the fiscal year ended December 31, 1998, its executive
officers and directors and Blue Cross complied with all applicable Section 16(a)
filing requirements.
 
                                    AUDITORS
 
    The Audit Committee of the Board of Directors has selected Ernst & Young LLP
as independent auditors for the Company for the year ended December 31, 1998.
Ernst & Young has examined the accounts of the Company since 1988.
Representatives of Ernst & Young will be present at the Meeting, will be
available to respond to questions and may make a statement if they so desire.
 
                                 OTHER MATTERS
 
    The Company knows of no other matters to come before the Meeting. If any
other matters properly come before the Meeting, it is the intention of the
persons acting pursuant to the accompanying appointment of proxy form to vote
the shares represented thereby in accordance with their best judgment.
 
                             SHAREHOLDER PROPOSALS
 
    Shareholder proposals for the 2000 Annual Meeting of Shareholders of the
Company must be received no later than December 15, 1999, at the Company's
principal executive offices, 3100 AMS Boulevard, Green Bay, Wisconsin 54313,
directed to the attention of the Secretary, in order to be considered for
inclusion in next year's annual meeting proxy material under the Securities and
Exchange Commission's proxy rules.
 
                                       28
<PAGE>
    Under the Company's Bylaws, written notice of shareholder proposals for the
2000 Annual Meeting of Shareholders of the Company which are not intended to be
considered for inclusion in next year's proxy material (shareholder proposals
submitted outside the processes of SEC Rule 14a-8) must be received no later
than February 13, 2000, and no earlier than January 14, 2000, at the Company's
offices, directed to the attention of the Secretary, and such notice must
contain the information specified in the Company's Bylaws.
 
                                          AMERICAN MEDICAL SECURITY GROUP, INC.
 
                                                   [SIGNATURE]
 
                                          Timothy J. Moore
                                          SECRETARY
 
Green Bay, Wisconsin
 
April 14, 1999
 
A COPY (WITHOUT EXHIBITS) OF THE COMPANY'S ANNUAL REPORT ON FORM 10-K FOR THE
YEAR ENDED DECEMBER 31, 1998, WILL BE PROVIDED WITHOUT CHARGE TO EACH RECORD OR
BENEFICIAL OWNER OF THE COMPANY'S COMMON STOCK AS OF MARCH 24, 1999, ON THE
WRITTEN REQUEST OF SUCH PERSON DIRECTED TO: TIMOTHY J. MOORE, SECRETARY,
AMERICAN MEDICAL SECURITY GROUP, INC., 3100 AMS BOULEVARD, GREEN BAY, WISCONSIN
54313.
 
                                       29
<PAGE>
                                                                      APPENDIX A
 
                             EQUITY INCENTIVE PLAN
                     AMERICAN MEDICAL SECURITY GROUP, INC.
                                 FEBRUARY 1993
                    (AS AMENDED AND RESTATED MARCH 15, 1999)
<PAGE>
                     AMERICAN MEDICAL SECURITY GROUP, INC.
                             EQUITY INCENTIVE PLAN
                    (AS AMENDED AND RESTATED MARCH 15, 1999)
 
                               TABLE OF CONTENTS
 
<TABLE>
<CAPTION>
                                                                                                               PAGE
                                                                                                            -----------
<C>        <S>                                                                                              <C>
 
ARTICLE 1. ESTABLISHMENT, PURPOSE AND DURATION............................................................           1
      1.1  Establishment of the Plan......................................................................           1
      1.2  Purpose of the Plan............................................................................           1
      1.3  Duration of the Plan...........................................................................           1
 
ARTICLE 2. DEFINITIONS....................................................................................           1
 
ARTICLE 3. ADMINISTRATION.................................................................................           4
      3.1  The Committee..................................................................................           4
      3.2  Authority of the Committee.....................................................................           4
      3.3  Decisions Binding..............................................................................           5
 
ARTICLE 4. SHARES SUBJECT TO THE PLAN.....................................................................           5
      4.1  Number of Shares...............................................................................           5
      4.2  Lapsed Awards..................................................................................           5
      4.3  Adjustments in Authorized Shares...............................................................           5
 
ARTICLE 5. ELIGIBILITY AND PARTICIPATION..................................................................           6
      5.1  Eligibility....................................................................................           6
      5.2  Actual Participation...........................................................................           6
 
ARTICLE 6. STOCK OPTIONS..................................................................................           6
      6.1  Grant of Options...............................................................................           6
      6.2  Option Award Agreement.........................................................................           6
      6.3  Option Price...................................................................................           6
      6.4  Duration of Options............................................................................           6
      6.5  Exercise of Options............................................................................           6
      6.6  Payment........................................................................................           6
      6.7  Restrictions on Share Transferability..........................................................           7
      6.8  Termination of Employment Due to Death, Disability or Retirement...............................           7
      6.9  Termination of Employment for Other Reasons....................................................           7
     6.10  Exercise of Options With Respect to Directors..................................................           8
     6.11  Restrictions on Transferability................................................................           8
 
ARTICLE 7. STOCK APPRECIATION RIGHTS......................................................................           8
      7.1  Grant of SARs..................................................................................           8
      7.2  Exercise of Tandem SARs........................................................................           8
      7.3  Exercise of Affiliated SARs....................................................................           8
      7.4  Exercise of Freestanding SARs..................................................................           9
      7.5  SAR Agreement..................................................................................           9
      7.6  Term of SARs...................................................................................           9
      7.7  Payment of SAR Amount..........................................................................           9
      7.8  Rule 16b-3 Requirements........................................................................           9
      7.9  Termination of Employment Due to Death, Disability, or Retirement..............................           9
     7.10  Termination of Employment for Other Reasons....................................................          10
     7.11  Exercise of SARs With Respect to Directors.....................................................          10
     7.12  Non-transferability of SARs....................................................................          10
</TABLE>
 
                                      A-i
<PAGE>
 
<TABLE>
<CAPTION>
                                                                                                               PAGE
                                                                                                            -----------
 
<C>        <S>                                                                                              <C>
ARTICLE 8. RESTRICTED STOCK...............................................................................          10
      8.1  Grant of Restricted Stock......................................................................          10
      8.2  Restricted Stock Agreement.....................................................................          10
      8.3  Transferability................................................................................          10
      8.4  Other Restrictions.............................................................................          10
      8.5  Certificate Legend.............................................................................          11
      8.6  Removal of Restrictions........................................................................          11
      8.7  Voting Rights..................................................................................          11
      8.8  Dividends and Other Distributions..............................................................          11
      8.9  Termination of Employment Due to Death, Disability, or Retirement..............................          11
     8.10  Termination of Employment for Other Reasons....................................................          11
     8.11  Restricted Stock Granted to Directors..........................................................          11
 
ARTICLE 9. PERFORMANCE UNITS AND PERFORMANCE SHARES.......................................................          11
      9.1  Grant of Performance Units/Shares..............................................................          11
      9.2  Value of Performance Units/Shares..............................................................          12
      9.3  Earning of Performance Units/Shares............................................................          12
      9.4  Form and Timing of Payment of Performance Units/Shares.........................................          12
           Termination of Employment Due to Death, Disability, Retirement, or Involuntary Termination               12
      9.5  (Without Cause)................................................................................
      9.6  Termination of Employment for Other Reasons....................................................          12
      9.7  Performance Units/Shares Granted to Directors..................................................          12
      9.8  Non-transferability............................................................................          12
 
ARTICLE 10. BENEFICIARY DESIGNATION.......................................................................          13
 
ARTICLE 11. DEFERRALS.....................................................................................          13
 
ARTICLE 12. RIGHTS OF EMPLOYEES...........................................................................          13
     12.1  Employment.....................................................................................          13
     12.2  Participation..................................................................................          13
 
ARTICLE 13. CHANGE IN CONTROL.............................................................................          13
 
ARTICLE 14. AMENDMENT, MODIFICATION, AND TERMINATION......................................................          14
     14.1  Amendment, Modification and Termination........................................................          14
     14.2  Awards Previously Granted......................................................................          14
 
ARTICLE 15. WITHHOLDING...................................................................................          14
     15.1  Tax Withholding................................................................................          14
     15.2  Share Withholding..............................................................................          14
 
ARTICLE 16. INDEMNIFICATION...............................................................................          14
 
ARTICLE 17. SUCCESSORS....................................................................................          14
 
ARTICLE 18. LEGAL CONSTRUCTION............................................................................          15
     18.1  Gender and Number..............................................................................          15
     18.2  Severability...................................................................................          15
     18.3  Requirements of Law............................................................................          15
     18.4  Securities Law Compliance......................................................................          15
     18.4  Governing Law..................................................................................          15
</TABLE>
 
                                      A-ii
<PAGE>
                     AMERICAN MEDICAL SECURITY GROUP, INC.
                             EQUITY INCENTIVE PLAN
                    (AS AMENDED AND RESTATED MARCH 15, 1999)
 
                 ARTICLE 1. ESTABLISHMENT, PURPOSE AND DURATION
 
    1.1  ESTABLISHMENT OF THE PLAN.  American Medical Security Group, Inc., a
Wisconsin corporation formerly known as United Wisconsin Services, Inc. (the
"Company"), established this incentive compensation plan known as the "American
Medical Security Group, Inc. Equity Incentive Plan" (herein referred to as the
"Plan") effective as of February 24, 1993 (the "Effective Date") upon approval
by its Board of Directors, and ratification by an affirmative vote of a majority
of Shares at an annual shareholders' meeting of the Company. (The validity of
any awards granted prior to shareholder ratification of the Plan were contingent
upon such ratification.)
 
    The Plan, as set forth in this document, remains in effect as provided in
Section 1.3 herein and permits the grant of Non-qualified Stock Options
("NQSOs"), Incentive Stock Options ("ISOs"), Stock Appreciation Rights ("SARs"),
Restricted Stock, Performance Units, and Performance Shares.
 
    1.2  PURPOSE OF THE PLAN.  The purpose of the Plan is to promote the
success, and enhance the value, of the Company by linking the personal interests
of Participants to those of Company shareholders, and by providing Participants
with an incentive for outstanding performance.
 
    The Plan is further intended to provide flexibility to the Company in its
ability to motivate, attract, and retain the services of Participants upon whose
judgment, interest, and special effort the successful conduct of its operation
is dependent.
 
    1.3  DURATION OF THE PLAN.  Subject to approval by the Board of Directors of
the Company and ratification by the shareholders of the Company, the Plan
commenced on the Effective Date, as described in Section 1.1 herein, and shall
remain in effect, subject to the right of the Board of Directors of the Company
to terminate the Plan at any time pursuant to Article 14 herein, until all
Shares subject to it shall have been purchased or acquired according to the
Plan's provisions. However, to the extent required by the Internal Revenue Code,
no ISO may be granted under the Plan on a date that is more than ten years from
the date the Plan is adopted, or, if earlier, the date the Plan is approved by
shareholders.
 
                             ARTICLE 2. DEFINITIONS
 
    Whenever used in the Plan, the following terms shall have the meanings set
forth below and when the meaning is intended, the initial letter of the word is
capitalized:
 
        (a) "AFFILIATE" means a company closely related to American Medical
    Security Group, Inc. which is designated as an Affiliate by the Board. For
    purposes of this Plan, United Wisconsin Services, Inc. (f/k/a Newco/UWS,
    Inc.) and Blue Cross & Blue Shield United of Wisconsin shall each be
    considered an Affiliate only with respect to Stock Options issued prior to
    September 11, 1998.
 
        (b) "AFFILIATED SAR" means an SAR that is granted in connection with a
    related Option, and which will be deemed to automatically be exercised
    simultaneous with the exercise of the related Option.
 
        (c) "AWARD" means, individually or collectively, a grant under this Plan
    of Non-qualified Stock Options, Incentive Stock Options, Stock Appreciation
    Rights, Restricted Stock, Performance Units, or Performance Shares.
 
        (d) "AWARD AGREEMENT" means an agreement entered into by each
    Participant and the Company, setting forth the terms and provisions
    applicable to Awards granted to Participants under this Plan.
 
                                      A-1
<PAGE>
        (e) "BENEFICIAL OWNER" shall have the meaning ascribed to such term in
    Rule 13d-3 of the General Rules and Regulations under the Exchange Act.
 
        (f) "BOARD" or "BOARD OF DIRECTORS" means the Board of Directors of the
    Company.
 
        (g) "CAUSE" means:
 
           (i) willful and gross misconduct on the part of a Participant that is
           materially and demonstrably detrimental to the Company; or
 
           (ii) the commission by a Participant of one or more acts which
           constitute an indictable crime under United States Federal, state, or
           local law. "Cause" under either (i) or (ii) shall be determined in
           good faith by the Committee.
 
        (h) "CHANGE IN CONTROL" of the Company in connection with any Award
    Agreement entered into before March 15, 1999 shall mean a "Change in
    Control" as defined in the Plan prior to its amendment and restatement on
    March 15, 1999 and "Change in Control" of the Company in connection with any
    Award Agreement entered into on or after March 15, 1999 shall be deemed to
    have occurred as of the date that:
 
           (i) a majority of Directors of the Company cease to continue to serve
           as Directors of the Company and the Chief Executive Officer of the
           Company ceases to serve as the Chief Executive of the Company as the
           direct or indirect result of, or in connection with the occurrence
           of:
 
               (a) any person, including a "group" as defined in Section
               13(d)(3) of the Securities Exchange Act of 1934, becoming,
               directly or indirectly, the beneficial owner of securities of the
               Company, or any other subsidiary, representing forty percent
               (40%) or more of the combined voting power of the then
               outstanding securities of the Company that may be cast for the
               election of Directors of the Company (other than as a result of
               an issuance of securities initiated by the Company or open market
               purchases approved by the Board of Directors of the Company as
               long as the majority of the Directors at the time of such
               approval are also Directors at the time the purchases are made);
 
               (b) a cash tender or exchange offer;
 
               (c) a hostile or involuntary merger or other business
           combination;
 
               (d) a sale of all or substantially all assets of the Company;
 
               (e) a contested election of directors; or
 
               (f) any combination of the aforementioned events; or
 
           (ii) the shareholders approve a plan of liquidation or dissolution of
       the Company.
 
        (i) "CODE" means the Internal Revenue Code of 1986, as amended from time
    to time.
 
        (j) "COMMITTEE" means the Compensation Committee of American Medical
    Security Group, Inc., as appointed by the Board to administer the Plan, or
    such other committee as may be appointed by the Board consistent with
    Section 3.1.
 
        (k) "COMPANY" means American Medical Security Group, Inc., a Wisconsin
    corporation or any successor thereto as provided in Article 17 herein.
 
        (l) "COVERED EMPLOYEE" means a Participant designated prior to the grant
    of an award of Restricted Stock, Performance Units, or Performance Shares by
    the Committee who is or may be a "covered employee" within the meaning of
    Section 162(m)(3) of the Internal Revenue Code in the
 
                                      A-2
<PAGE>
    year in which such Restricted Stock, Performance Units or Performance Awards
    are taxable to such Participant.
 
        (m) "DIRECTOR" means any individual who is a member of the Board of
    Directors of the Company or any Subsidiary or Affiliate.
 
        (n) "DISABILITY" means with respect to any ISOs, a permanent and total
    disability within the meaning of Code Section 22(e)(3), and with respect to
    all other Awards under the Plan, a medically determinable mental or physical
    impairment which renders a Participant totally and presumably permanently
    unable to continue in employment with the Company and all Affiliates. The
    determination of disability shall be made by the Committee in good faith,
    upon receipt of sufficient competent medical advice from one or more
    individuals, selected by the Committee, who are qualified to give
    professional medical advice.
 
        (o) "EMPLOYEE" means any full-time employee of the Company or of the
    Company's Subsidiaries or Affiliates.
 
        (p) "EXCHANGE ACT" means the Securities Exchange Act of 1934, as amended
    from time to time, or any successor Act thereto.
 
        (q) "FAIR MARKET VALUE" means the closing price for Shares on the
    relevant date, or (if there were no sales on such date) the average of
    closing prices on the nearest day before and the nearest day after the
    relevant date, on a stock exchange or over the counter, as determined by the
    Committee.
 
        (r) "FREESTANDING SAR" means an SAR that is granted independently of any
    Options.
 
        (s) "INCENTIVE STOCK OPTION" or "ISO" means an option to purchase
    Shares, granted under Article 6 herein, which is designated as an Incentive
    Stock Option and is intended to meet the requirements of Section 422 of the
    Code.
 
        (t) "INSIDER" shall mean an Employee or Participant who is, on the
    relevant date, an officer, director of the Company, as defined in Rule 16
    under the Exchange Act.
 
        (u) "NON-QUALIFIED STOCK OPTION" or "NQSO" means an option to purchase
    Shares, granted under Article 6 herein, which is not intended to be an
    Incentive Stock Option.
 
        (v) "OPTION" means an Incentive Stock Option or a Non-qualified Stock
    Option.
 
        (w) "OPTION PRICE" means the price at which a Share may be purchased by
    a Participant pursuant to an Option, as determined by the Committee.
 
        (x) "PARTICIPANT" means a person who has outstanding an Award granted
    under the Plan.
 
        (y) "PERFORMANCE GOALS" means the performance goals established by the
    Committee prior to the grant of any Award of Restricted Stock, Performance
    Units, or Performance Shares that are based on the attainment of goals
    relating to one or more of the following business criteria measured on an
    absolute basis or in terms of growth or reduction: net income (pre-tax or
    after-tax and with adjustments as stipulated), earnings per share, return on
    equity, return on assets, return on tangible book value, operating income,
    earnings before depreciation, interest, taxes and amortization (EBDITA),
    loss ratio, expense ratio, increase in stock price, total shareholder
    return, economic value added and operating cash flow. With respect to
    Covered Employees, all Performance Goals shall be objective performance
    goals satisfying the requirements for "performance-based compensation"
    within the meaning of Section 162(m)(4) of the Internal Revenue Code and
    shall be established by the Committee within the time prescribed by Section
    162(m) of such Code and related regulations. With respect to Participants
    who are not Covered Employees, the Committee may establish other subjective
    or objective performance goals, including individual goals, which it deems
    appropriate.
 
                                      A-3
<PAGE>
        (z) "PERFORMANCE UNIT" means an Award granted to a Participant, as
    described in Article 9 herein.
 
        (aa) "PERFORMANCE SHARE" means an Award granted to a Participant, as
    described in Article 9 herein.
 
        (bb) "PERIOD OF RESTRICTION" means the period during which the transfer
    of Shares of Restricted Stock is limited in some way (based on the passage
    of time, the achievement of Performance Goals, or upon the occurrence of
    other events as determined by the Committee, at its discretion), and the
    Shares are subject to a substantial risk of forfeiture, as provided in
    Article 8 herein.
 
        (cc) "PERSON" shall have the meaning ascribed to such term in Section
    3(a)(9) of the Exchange Act and used in Sections 13(d) and 14(d) thereof,
    including a "group" as defined in Section 13(d).
 
        (dd) "RESTRICTED STOCK" means an Award granted to a Participant pursuant
    to Article 8 herein.
 
        (ee) "RETIREMENT" shall have the meaning ascribed to it under the
    Company's tax qualified retirement plan.
 
        (ff) "SHARES" means the shares of common stock of the Company.
 
        (gg) "SUBSIDIARY" means any corporation in which the Company owns
    directly, or indirectly through subsidiaries, at least fifty percent (50%)
    of the total combined voting power of all classes of stock, or any other
    entity (including, but not limited to, partnerships and joint ventures) in
    which the Company owns at least fifty percent (50%) of the combined equity
    thereof.
 
        (hh) "STOCK APPRECIATION RIGHT" or "SAR" means an Award, granted alone
    or in connection with a related Option, designated as an SAR, pursuant to
    the terms of Article 7 herein.
 
        (ii) "TANDEM SAR" means an SAR that is granted in connection with a
    related Option, the exercise of which shall require forfeiture of the right
    to purchase a Share under the related Option (and when a Share is purchased
    under the Option, an SAR shall similarly be canceled).
 
        (jj) "WINDOW PERIOD" means a window period of time as defined in the
    Company's then current insider trading policy.
 
                           ARTICLE 3. ADMINISTRATION
 
    3.1  THE COMMITTEE.  The Plan shall be administered by the Compensation
Committee of the Board of American Medical Security Group, Inc., or by any other
Committee appointed by the Board consisting of not less than two (2) Directors
who are not Employees. The members of the Committee shall be appointed from time
to time by, and shall serve at the discretion of, the Board of Directors.
 
    It is intended that at all times, the Committee shall be comprised solely of
Directors who are both: (i) Non-Employee Directors, as defined in Rule 16b-3
under the Exchange Act; and (ii) Outside Directors, as defined in Treas. Reg.
1.162-27. However, the failure to so comply with Rule 16b-3 and/or Treas. Reg.
1.162-27 shall not affect the validity of any Awards made by the Committee in
accordance with the provisions of the Plan.
 
    3.2  AUTHORITY OF THE COMMITTEE.  The Committee shall have full power except
as limited by law or by the Articles of Incorporation or By-laws of the Company,
and subject to the provisions herein, to determine the size and types of Awards;
to determine the terms and conditions of such Awards in a manner consistent with
the Plan; to construe and interpret the Plan and any agreement or instrument
entered into under the Plan; to establish, amend, or waive rules and regulations
for the Plan's administration; and (subject to the provisions of Article 14
herein) to amend the terms and conditions of any outstanding Award to the extent
such terms and conditions are within the discretion of the Committee as provided
in the Plan. Further, the Committee shall make all other determinations which
may be necessary
 
                                      A-4
<PAGE>
or advisable for the administration of the Plan. As permitted by law, the
Committee may delegate its authority as identified hereunder.
 
    3.3  DECISIONS BINDING.  All determinations and decisions made by the
Committee pursuant to the provisions of the Plan and all related orders or
resolutions of the Board of Directors shall be final, conclusive, and binding on
all Persons, including the Company, its stockholders, Employees, Participants,
and their estates and beneficiaries.
 
                     ARTICLE 4. SHARES SUBJECT TO THE PLAN
 
    4.1  NUMBER OF SHARES.  Subject to adjustment as provided in Section 4.3
herein, the total number of Shares available for grant under the Plan may not
exceed 4,000,000. These 4,000,000 Shares may be either authorized but unissued
or reacquired Shares.
 
    The following rules will apply for purposes of the determination of the
number of Shares available for grant under the Plan:
 
        (a) While an Award is outstanding, it shall be counted against the
    authorized pool of Shares, regardless of its vested status.
 
        (b) The grant of an Option or Restricted Stock shall reduce the Shares
    available for grant under the Plan by the number of Shares subject to such
    Award.
 
        (c) The grant of a Tandem SAR shall reduce the number of Shares
    available for grant by the number of Shares subject to the related Option
    (i.e., there is no double counting of Options and their related Tandem
    SARs).
 
        (d) The grant of an Affiliated SAR shall reduce the number of Shares
    available for grant by the number of Shares subject to the SAR, in addition
    to the number of Shares subject to the related Option.
 
        (e) The grant of a Freestanding SAR shall reduce the number of Shares
    available for grant by the number of Freestanding SARs granted.
 
        (f) The Committee shall in each case determine the appropriate number of
    Shares to deduct from the authorized pool in connection with the grant of
    Performance Units and/or Performance Shares.
 
        (g) To the extent that an Award is settled in cash rather than in
    Shares, the authorized Share pool shall be credited with the appropriate
    number of Shares represented by the cash settlement of the Award, as
    determined at the sole discretion of the Committee (subject to the
    limitation set forth in Section 4.2 herein).
 
    The maximum number of Shares with respect to which Awards may be made to any
Participant annually (in any one calendar year) shall not exceed 250,000 shares.
Notwithstanding the foregoing, if the Participant receives the Award prior to
March 31, 1997 in connection with the Employee's initial employment by the
Company or in connection with a merger or acquisition by the Company, the
maximum number of Shares with respect to which Awards may be made during the
three (3) year period ended March 31, 1997 shall be 850,000 Shares. No
Participant may be granted Performance Units in any one calendar year that when
payable would exceed $3,000,000.
 
    4.2  LAPSED AWARDS.  If any Award granted under this Plan is canceled,
terminates, expires, or lapses for any reason (with the exception of the
termination of a Tandem SAR upon exercise of the related Option, or the
termination of a related Option upon exercise of the corresponding Tandem SAR),
any Shares subject to such Award again shall be available for the grant of an
Award under the Plan.
 
    4.3  ADJUSTMENTS IN AUTHORIZED SHARES.  In the event of any merger,
reorganization, consolidation, recapitalization, separation, liquidation, stock
dividend, split-up, Share combination, or other change in the
 
                                      A-5
<PAGE>
corporate structure of the Company affecting the Shares, such adjustment shall
be made in the number or class of Shares which may be delivered under the Plan,
and in the number and class of and/or price of Shares subject to outstanding
Options, SARs, and Restricted Stock granted under the Plan, as may be determined
to be appropriate and equitable by the Committee, in its sole discretion, to
prevent dilution or enlargement of rights; and provided that the number of
Shares subject to any Award shall always be a whole number.
 
                    ARTICLE 5. ELIGIBILITY AND PARTICIPATION
 
    5.1  ELIGIBILITY.  Persons eligible to participate in this Plan include all
Directors and all full-time, active Employees of the Company, its Subsidiaries
and Affiliates, as determined by the Committee.
 
    5.2  ACTUAL PARTICIPATION.  Subject to the provisions of the Plan, the
Committee may, from time to time, select from all eligible Participants, those
to whom Awards shall be granted and shall determine the nature and amount of
each award.
 
                            ARTICLE 6. STOCK OPTIONS
 
    6.1  GRANT OF OPTIONS.  Subject to the terms and provisions of the Plan,
Options may be granted to Participants at any time and from time to time as
shall be determined by the Committee. The Committee shall have discretion in
determining the number of Shares subject to Options granted to each Participant.
The Committee may grant ISOs, NQSOs, or a combination thereof.
 
    If required by applicable tax rules regarding a particular grant of ISOs, to
the extent that the aggregate fair market value (determined as of the date an
ISO is granted) of Shares with respect to which ISOs are exercisable for the
first time by a Participant during any calendar year exceeds $100,000 (or such
other limit as prescribed by the Code) such option grant shall be treated as a
grant of NQSOs rather than ISOs.
 
    6.2  OPTION AWARD AGREEMENT.  Each Option grant shall be evidenced by an
Option Award Agreement that shall specify the Option Price, the duration of the
Option, the number of Shares to which the Option pertains, and such other
provisions as the Committee shall determine. The Option Award Agreement also
shall specify whether the Option is intended to be an ISO within the meaning of
Section 422 of the Code, or an NQSO whose grant is intended not to fall under
the Code provisions of Section 422.
 
    6.3  OPTION PRICE.  The Option Price for each grant of an Option shall be
determined by the Committee; provided that the Option Price shall not be less
than one hundred percent (100%) of the Fair Market Value of a Share on the date
the Option is granted.
 
    6.4  DURATION OF OPTIONS.  Each Option shall expire at such time as the
Committee shall determine at the time of grant; provided, however, that no ISO
shall be exercisable later than the tenth (10th) anniversary date of its grant,
and no NQSO shall be exercisable later than the twelfth (12th) anniversary date
of its grant.
 
    6.5  EXERCISE OF OPTIONS.  Options granted under the Plan shall be
exercisable at such times and be subject to such restrictions and conditions as
the Committee shall in each instance approve, which need not be the same for
each grant or for each Participant. However, in no event may any Option granted
under this Plan become exercisable prior to six (6) months following the date of
its grant.
 
    6.6  PAYMENT.  Options shall be exercised by the delivery of a written
notice of exercise to the Secretary of the Company, setting forth the number of
Shares with respect to which the Option is to be exercised, accompanied by
payment in full of the Option Price.
 
    The Option Price upon exercise of any Option shall be payable to the Company
in full either: (a) in cash or its equivalent, or (b) by tendering previously
acquired Shares having an aggregate Fair Market
 
                                      A-6
<PAGE>
Value at the time of exercise equal to the total Option Price (provided that the
Shares which are tendered must have been held by the Participant for at least
six (6) months prior to their tender to satisfy the Option Price), or (c) by a
combination of (a) and (b).
 
    The Committee also may allow cashless exercise as permitted under Federal
Reserve Board's Regulation T, subject to applicable securities law restrictions,
or by any other means which the Committee determines to be consistent with the
Plan's purpose and applicable law.
 
    As soon as practicable after receipt of a written notification of exercise
and full payment, the Company shall deliver to the Participant, in the
Participant's name, Share certificates in an appropriate amount based upon the
number of Shares purchased under the Option(s).
 
    6.7  RESTRICTIONS ON SHARE TRANSFERABILITY.  The Committee may impose such
restrictions on any Shares acquired pursuant to the exercise of an Option under
the Plan, as it may deem advisable, including, without limitation, restrictions
under applicable Federal securities laws, under the requirements of any Stock
exchange or market upon which such Shares are then listed and/or traded, and
under any Blue Sky or state securities laws applicable to such Shares.
 
    6.8  TERMINATION OF EMPLOYMENT DUE TO DEATH, DISABILITY OR RETIREMENT.
 
        (a) TERMINATION BY DEATH. In the event the employment of a Participant
    is terminated by reason of death, all outstanding Options granted to that
    Participant shall immediately vest one hundred percent (100%), and shall
    remain exercisable at any time prior to their expiration date, or for one
    (1) year after the date of death, whichever period is shorter, by such
    person or persons as shall have been named as the Participant's beneficiary,
    or by such persons that have acquired the Participant's rights under the
    Option by will or by the laws of descent and distribution.
 
        (b) TERMINATION BY DISABILITY. In the event the employment of a
    Participant is terminated by reason of Disability, all outstanding Options
    granted to that Participant shall immediately vest one hundred percent
    (100%) as of the date the Committee determines the definition of Disability
    to have been satisfied, and shall remain exercisable at any time prior to
    their expiration date, or for one (1) year after the date that the Committee
    determines the definition of Disability to have been satisfied, whichever
    period is shorter.
 
        (c) TERMINATION BY RETIREMENT. In the event the employment of a
    Participant is terminated by reason of Retirement, the Committee shall
    retain discretion over the treatment of Options.
 
        (d) EMPLOYMENT TERMINATION FOLLOWED BY DEATH. In the event that a
    Participant's employment terminates by reason of Disability or Retirement,
    and within the exercise period allowed by the Committee following such
    termination the Participant dies, then the remaining exercise period under
    outstanding Options shall equal the longer of: (i) one (1) year following
    death; or (ii) the remaining portion of the exercise period which was
    triggered by the employment termination. Such Options shall be exercisable
    by such person or persons who shall have been named as the Participant's
    beneficiary, or by such persons who have acquired the Participant's rights
    under the Option by will or by the laws of descent and distribution.
 
        (e) EXERCISE LIMITATIONS ON ISOS. In the case of ISOs, the tax treatment
    prescribed under Section 422 of the Internal Revenue Code of 1986, as
    amended, may not be available if the Options are not exercised within the
    Section 422 prescribed time periods after each of the various types of
    employment termination.
 
    6.9  TERMINATION OF EMPLOYMENT FOR OTHER REASONS.  If the employment of a
Participant shall terminate for any reason other than the reasons set forth in
Section 6.8 (and other than for Cause), all Options held by the Participant
which are not vested as of the effective date of employment termination
immediately shall be forfeited to the Company (and shall once again become
available for grant under the
 
                                      A-7
<PAGE>
Plan). However, the Committee, in its sole discretion, shall have the right to
immediately vest all or any portion of such Options, subject to such terms as
the Committee, in its sole discretion, deems appropriate.
 
    Options which are vested as of the effective date of employment termination
may be exercised by the Participant for a period of up to six (6) months
following termination, or for such longer period up to one (1) year as the
Committee determines with respect to a particular Participant.
 
    If the employment of a Participant shall be terminated by the Company for
Cause, all outstanding options held by the Participant immediately shall be
forfeited to the Company and no additional exercise period shall be allowed,
regardless of the vested status of the Option.
 
    For purposes of this Section and Section 6.8, a termination of employment
shall occur only after the Employee ceases to be an Employee of the Company and
all Subsidiaries or Affiliates.
 
    6.10  EXERCISE OF OPTIONS WITH RESPECT TO DIRECTORS.  Options granted to
Directors shall be exercisable at such times and be subject to such restrictions
and conditions as the Committee shall in each instance approve, which need not
be the same for each grant or for each such Participant. However, in no event
may any such Option become exercisable prior to six (6) months following the
date of its grant.
 
    6.11  RESTRICTIONS ON TRANSFERABILITY.  No Option granted under the Plan may
be sold, transferred, pledged, assigned or otherwise alienated or hypothecated,
other than by will or by the laws of descent and distribution, and shall be
exercisable by a Participant during his or her lifetime only by the Participant
except that NQSOs may be transferred by a Participant to the Participant's
spouse, children or grandchildren or to a trust for the benefit of such spouse,
children or grandchildren.
 
                      ARTICLE 7. STOCK APPRECIATION RIGHTS
 
    7.1  GRANT OF SARS.  Subject to the terms and conditions of the Plan, an SAR
may be granted to a Participant at any time and from time to time as shall be
determined by the Committee. The Committee may grant Affiliated SARs,
Freestanding SARs, Tandem SARs, or any combination of these forms of SAR.
 
    The Committee shall have complete discretion in determining the number of
SARs granted to each Participant (subject to Article 4 herein) and consistent
with the provisions of the Plan, in determining the terms and conditions
pertaining to such SARs. However, the grant price of a Freestanding SAR shall be
at least equal to one hundred percent (100%) of the Fair Market Value of a Share
on the date of grant of the SAR. The grant price of Tandem SARs or Affiliated
SARs shall equal the Option Price of the related Option. In no event shall any
SAR granted hereunder become exercisable within the first six (6) months of its
grant.
 
    7.2  EXERCISE OF TANDEM SARS.  Tandem SARs may be exercised for all or part
of the Shares subject to the related Option upon the surrender of the right to
exercise the equivalent portion of the related Option. A Tandem SAR may be
exercised only with respect to the Shares for which its related Option is then
exercisable.
 
    Notwithstanding any other provision of this Plan to the contrary, with
respect to a Tandem SAR granted in connection with an ISO: (i) the Tandem SAR
will expire no later than the expiration of the underlying ISO; (ii) the value
of the payout with respect to the Tandem SAR may be for no more than one hundred
percent (100%) of the difference between the Option Price of the underlying ISO
and the Fair Market Value of the Shares subject to the underlying ISO at the
time the Tandem SAR is exercised; and (iii) the Tandem SAR may be exercised only
when the Fair Market Value of the Shares subject to the ISO exceeds the Option
Price of the ISO.
 
    7.3  EXERCISE OF AFFILIATED SARS.  Affiliated SARs shall be deemed to be
exercised upon the exercise of the related Options. The deemed exercise of
Affiliated SARs shall not necessitate a reduction in the number of related
Options.
 
                                      A-8
<PAGE>
    7.4  EXERCISE OF FREESTANDING SARS.  Freestanding SARs may be exercised upon
whatever terms and conditions the Committee, in its sole discretion, imposes
upon them.
 
    7.5  SAR AGREEMENT.  Each SAR grant shall be evidenced by an Award Agreement
that shall specify the grant price, the term of the SAR, and such other
provisions as the Committee shall determine.
 
    7.6  TERM OF SARS.  The term of an SAR granted under the Plan shall be
determined by the Committee, in its sole discretion; provided, however, that
such term shall not exceed twelve (12) years.
 
    7.7  PAYMENT OF SAR AMOUNT.  Upon exercise of an SAR, a Participant shall be
entitled to receive payment from the Company in an amount determined by
multiplying:
 
        (a) The difference between the Fair Market Value of a Share on the date
    of exercise over the grant price; by
 
        (b) The number of Shares with respect to which the SAR is exercised.
 
    At the discretion of the Committee, the payment upon the exercise of an SAR
may be in cash, in Shares of equivalent value, or in some combination thereof.
 
    7.8  RULE 16B-3 REQUIREMENTS.  Notwithstanding any other provision of the
Plan, the Committee may impose such conditions on exercise of an SAR (including,
without limitation, the right of the Committee to limit the time of exercise to
specified periods) as may be required to satisfy the requirements of Section 16
(or any successor rule) of the Exchange Act.
 
    Further, unless the Committee determines otherwise, if the Participant is an
Insider, the ability of the Participant to exercise SARs for cash may be limited
to the Window Period or otherwise as provided in the Company's then current
insider trading policy.
 
    7.9  TERMINATION OF EMPLOYMENT DUE TO DEATH, DISABILITY, OR RETIREMENT.
 
        (a) TERMINATION BY DEATH. In the event the employment of a Participant
    is terminated by reason of death, all outstanding SARs granted to that
    Participant shall immediately vest one hundred percent (100%), and shall
    remain exercisable at any time prior to their expiration date, or for one
    (1) year after the date of death, whichever period is shorter, by such
    person or persons as shall have been named as the Participant's beneficiary,
    or by such persons that have acquired the Participant's rights under the SAR
    by will or by the laws of descent and distribution.
 
        (b) TERMINATION BY DISABILITY. In the event the employment of a
    Participant is terminated by reason of Disability, all outstanding SARs
    granted to that Participant shall immediately vest one hundred percent
    (100%) as of the date the Committee determines the definition of Disability
    to have been satisfied, and shall remain exercisable at any time prior to
    their expiration date, or for one (1) year after the date that the Committee
    determines the definition of Disability to have been satisfied, whichever
    period is shorter.
 
        (c) TERMINATION BY RETIREMENT. In the event the employment of a
    Participant is terminated by reason of Retirement, the Committee shall
    retain discretion over the treatment of SARs.
 
        (d) EMPLOYMENT TERMINATION FOLLOWED BY DEATH. In the event that a
    Participant's employment terminates by reason of Disability or Retirement,
    and within the exercise period allowed by the Committee following such
    termination, the Participant dies, then the remaining exercise period under
    outstanding SARs shall equal the longer of: (i) one (1) year following
    death; or (ii) the remaining portion of the exercise period which was
    triggered by the employment termination. Such SARs shall be exercisable by
    such person or persons who shall have been named as the Participant's
    beneficiary, or by such persons who have acquired the Participant's rights
    under the SAR by will or by the laws of descent and distribution.
 
                                      A-9
<PAGE>
    7.10  TERMINATION OF EMPLOYMENT FOR OTHER REASONS.  If the employment of a
Participant shall terminate for any reason other than the reasons set forth in
Section 7.9 (and other than for Cause), all SARs held by the Participant which
are not vested as of the effective date of employment termination immediately
shall be forfeited to the Company (and shall once again become available for
grant under the Plan). However, the Committee, in its sole discretion, shall
have the right to immediately vest all or any portion of such SARs, subject to
such terms as the Committee, in its sole discretion, deems appropriate.
 
    SARs which are vested as of the effective date of employment termination may
be exercised by the Participant within the period beginning on the effective
date of employment termination, and ending six (6) months after such date.
 
    If the employment of a Participant shall be terminated by the Company for
Cause, all outstanding SARs held by the Participant immediately shall be
forfeited to the Company and no additional exercise period shall be allowed,
regardless of the vested status of the SARs.
 
    7.11  EXERCISE OF SARS WITH RESPECT TO DIRECTORS.  SARs granted to Directors
may be exercised upon whatever terms and conditions the Committee, in its sole
discretion, imposes on them.
 
    7.12  NON-TRANSFERABILITY OF SARS.  No SAR granted under the Plan may be
sold, transferred, pledged, assigned, or otherwise alienated or hypothecated,
other than by will or by the laws of descent and distribution. Further, all SARs
granted to a Participant under the Plan shall be exercisable during his or her
lifetime only by such Participant.
 
                          ARTICLE 8. RESTRICTED STOCK
 
    8.1  GRANT OF RESTRICTED STOCK.  Subject to the terms and provisions of the
Plan, the Committee, at any time and from time to time, may grant Shares of
Restricted Stock to eligible Participants in such amounts as the Committee shall
determine.
 
    8.2  RESTRICTED STOCK AGREEMENT.  Each Restricted Stock grant shall be
evidenced by a Restricted Stock Agreement that shall specify the Period of
Restriction, or Periods, the number of Restricted Stock Shares granted, and such
other provisions as the Committee shall determine.
 
    8.3  TRANSFERABILITY.  Except as provided in this Article 8, the Shares of
Restricted Stock granted herein may not be sold, transferred, pledged, assigned,
or otherwise alienated or hypothecated until the end of the applicable Period of
Restriction established by the Committee and specified in the Restricted Stock
Agreement, or upon earlier satisfaction of any other conditions, as specified by
the Committee in its sole discretion and set forth in the Restricted Stock
Agreement. However, in no event may any Restricted Stock granted under the Plan
become vested in a Participant prior to six (6) months following the date of its
grant. All rights with respect to the Restricted Stock granted to a Participant
under the Plan shall be available during his or her lifetime only to such
Participant.
 
    8.4  OTHER RESTRICTIONS.  The Committee shall in the case of Covered
Employees, and may in the case of other Participants, condition the vesting of
Shares of Restricted Stock upon the attainment of Performance Goals established
before or at the time of the grant. The Committee may impose such other
restrictions on any Shares of Restricted Stock granted pursuant to the Plan as
it may deem advisable, and/or restrictions under applicable Federal or state
securities laws; and may legend the certificates representing Restricted Stock
to give appropriate notice of such restrictions. The provisions of Restricted
Stock Awards need not be the same with respect to each Participant.
 
                                      A-10
<PAGE>
    8.5  CERTIFICATE LEGEND.  In addition to any legends placed on certificates
pursuant to Section 8.4 herein, each certificate representing Shares of
Restricted Stock granted pursuant to the Plan shall bear the following legend:
 
        "The sale or other transfer of the Shares of stock represented by this
    certificate, whether voluntary, involuntary, or by operation of law, is
    subject to certain restrictions on transfer as set forth in the American
    Medical Security Group, Inc. Equity Incentive Plan, and in a Restricted
    Stock Agreement. A copy of the Plan and such Restricted Stock Agreement may
    be obtained from the Secretary of American Medical Security Group, Inc."
 
    8.6  REMOVAL OF RESTRICTIONS.  Except as otherwise provided in this Article
8, Shares of Restricted Stock covered by each Restricted Stock grant made under
the Plan shall become freely transferable by the Participant after the last day
of the Period of Restriction. Once the Shares are released from the
restrictions, the Participant shall be entitled to have the legend required by
Section 8.5 removed from his or her Share certificate.
 
    8.7  VOTING RIGHTS.  During the Period of Restriction, Participants holding
Shares of Restricted Stock granted hereunder may exercise full voting rights
with respect to those Shares.
 
    8.8  DIVIDENDS AND OTHER DISTRIBUTIONS.  During the Period of Restriction,
Participants holding Shares of Restricted Stock granted hereunder shall be
entitled to receive all dividends and other distributions paid with respect to
those Shares while they are so held. If any such dividends or distributions are
paid in Shares, the Shares shall be subject to the same restrictions on
transferability and forfeitability as the Shares of Restricted Stock with
respect to which they were paid.
 
    8.9  TERMINATION OF EMPLOYMENT DUE TO DEATH, DISABILITY, OR RETIREMENT.  In
the event the employment of a Participant is terminated by reason of death or
Disability, all outstanding Shares of Restricted Stock shall immediately vest
one hundred percent (100%) as of the date of employment termination (in the case
of Disability, the date employment terminates shall be deemed to be the date
that the Committee determines the definition of Disability to have been
satisfied). The Committee retains discretion over the treatment of Restricted
Stock upon Retirement. In the event of full vesting, the holder of the
certificates of Restricted Stock shall be entitled to have any
non-transferability legends required under Sections 8.4 and 8.5 of this Plan
removed from the Share certificates.
 
    8.10  TERMINATION OF EMPLOYMENT FOR OTHER REASONS.  If the employment of a
Participant shall terminate for any reason other than those specifically set
forth in Section 8.9 herein, all Shares of Restricted Stock held by the
Participant which are not vested as of the effective date of employment
termination immediately shall be forfeited and returned to the Company (and,
subject to Section 4.2 herein, shall once again become available for grant under
the Plan).
 
    With the exception of a termination of employment for Cause, the Committee,
in its sole discretion, shall have the right to provide for lapsing of the
restrictions of Restricted Stock following employment termination, upon such
terms and provisions as it deems proper.
 
    8.11  RESTRICTED STOCK GRANTED TO DIRECTORS.  Restricted Stock granted to
Directors shall be subject to all of the provisions in this Article 8 other than
Section 8.9 and 8.10. The Committee, in its sole discretion, shall have the
right to provide for the lapsing of the restrictions on the Restricted Stock
following the Director's cessation of service as a director, upon such terms and
provisions as it deems proper.
 
              ARTICLE 9. PERFORMANCE UNITS AND PERFORMANCE SHARES
 
    9.1  GRANT OF PERFORMANCE UNITS/SHARES.  Subject to the terms of the Plan,
Performance Units and Performance Shares may be granted to eligible Participants
at any time and from time to time, as shall be determined by the Committee.
Subject to Section 4.1, the Committee shall have complete discretion in
determining the number of Performance Units and Performance Shares granted to
each Participant.
 
                                      A-11
<PAGE>
    9.2  VALUE OF PERFORMANCE UNITS/SHARES.  Each Performance Unit shall have an
initial value that is established by the Committee at the time of grant. Each
Performance Share shall have an initial value equal to the Fair Market Value of
a Share on the date of grant. The Committee shall set Performance Goals in its
discretion which, depending on the extent to which they are met, will determine
the number and/or value of Performance Units/Shares that will be paid out to the
Participants. The time period during which the Performance Goals must be met
shall be called a "Performance Period." Performance Periods shall, in all cases,
exceed six (6) months in length.
 
    9.3  EARNING OF PERFORMANCE UNITS/SHARES.  After the applicable Performance
Period has ended, the holder of Performance Units/Shares shall be entitled to
receive payout on the number of Performance Units/Shares earned by the
Participant over the Performance Period, to be determined as a function of the
extent to which the corresponding Performance Goals have been achieved.
 
    9.4  FORM AND TIMING OF PAYMENT OF PERFORMANCE UNITS/SHARES.  Payment of
earned Performance Units/Shares shall be made in a single lump sum, within
forty-five (45) calendar days following the close of the applicable Performance
Period. The Committee, in its sole discretion, may pay earned Performance
Units/Shares in the form of cash or in Shares (or in a combination thereof),
which have an aggregate Fair Market Value equal to the value of the earned
Performance Units/Shares at the close of the applicable Performance Period.
 
    Prior to the beginning of each Performance Period, Participants may elect to
defer the receipt of Performance Unit/Share payout upon such terms as the
Committee deems appropriate.
 
    9.5  TERMINATION OF EMPLOYMENT DUE TO DEATH, DISABILITY, RETIREMENT, OR
INVOLUNTARY TERMINATION (WITHOUT CAUSE).  In the event the employment of a
Participant is terminated by reason of death or Disability or involuntary
termination without Cause during a Performance Period, the Participant shall
receive a prorated payout of the Performance Units/Shares. The Committee retains
discretion over the treatment of Performance Units/Shares upon Retirement. Any
prorated payout shall be determined by the Committee, in its sole discretion,
and shall be based upon the length of time that the Participant held the
Performance Units/Shares during the Performance Period, and shall further be
adjusted based on the achievement of the pre-established Performance Goals.
 
    Timing of payment of earned Performance Units/Shares shall be determined by
the Committee at its sole discretion.
 
    9.6  TERMINATION OF EMPLOYMENT FOR OTHER REASONS.  In the event that a
Participant's employment terminates for any reason other than those reasons set
forth in Section 9.5 herein, all Performance Units/ Shares shall be forfeited by
the Participant to the Company, and shall once again be available for grant
under the Plan.
 
    9.7  PERFORMANCE UNITS/SHARES GRANTED TO DIRECTORS.  Performance Units and
Performance Shares granted to Directors shall be subject to all provisions of
this Article 9 other than Sections 9.5 and 9.6. The Committee, in is sole
discretion, shall have the right to provide for the treatment of Performance
Units/ Shares following the Director's cessation of services as a director, upon
such terms and conditions as it deems proper.
 
    9.8  NON-TRANSFERABILITY.  Performance Units/Shares may not be sold,
transferred, pledged, assigned, or otherwise alienated or hypothecated, other
than by will or by the laws of descent and distribution. Further a Participant's
rights under the Plan shall be exercisable during the Participant's lifetime
only by the Participant or the Participant's legal representative.
 
                                      A-12
<PAGE>
                      ARTICLE 10. BENEFICIARY DESIGNATION
 
    Each Participant under the Plan may, from time to time, name any beneficiary
or beneficiaries (who may be named contingently or successively) to whom any
benefit under the Plan is to be paid in case of his or her death before he or
she receives any or all of such benefit and who is eligible to exercise vested
Options and SARs in the event of the Participant's death prior to such exercise.
Each such designation shall revoke all prior designations by the same
Participant, shall be in the form prescribed by the Company and will be
effective only when any necessary spousal consent is obtained and filed by the
Participant in writing with the Secretary of the Company during the
Participant's lifetime. In the absence of any such designation, benefits
remaining unpaid at the Participant's death shall be paid to the Participant's
estate and any vested Options and/or SARs not previously exercised prior to the
Participant's death may be exercised by the administrator of the Participant's
estate.
 
                             ARTICLE 11. DEFERRALS
 
    The Committee may permit a Participant to defer such Participant's receipt
of the payment of cash or the delivery of Shares that would otherwise be due to
such Participant by virtue of the exercise of the Option or SAR, the lapse or
waiver of restrictions with respect to Restricted Stock, or the satisfaction of
any requirements or goals with respect to Performance Units/Shares. If any such
deferral election is required or permitted, the Committee shall, in its sole
discretion, establish rules and procedures for such payment deferrals.
 
                        ARTICLE 12. RIGHTS OF EMPLOYEES
 
    12.1  EMPLOYMENT.  Nothing in the Plan shall interfere with or limit in any
way the right of the Company to terminate any Participant's employment at any
time, nor confer upon any Participant any right to continue in the employ of the
Company.
 
    For purposes of the Plan, transfer of employment of a Participant between
the Company and any one of its Subsidiaries or Affiliates (or between
Subsidiaries and/or Affiliates) shall not be deemed a termination of employment.
 
    12.2  PARTICIPATION.  No Employee shall have the right to be selected to
receive an Award under this Plan, or having been so selected, to be selected to
receive a future Award.
 
                         ARTICLE 13. CHANGE IN CONTROL
 
    Upon the occurrence of a Change in Control, unless otherwise specifically
prohibited by the terms of Section 18, herein:
 
        (a) Any and all Options and SARs granted hereunder shall become
    immediately exercisable;
 
        (b) Any restriction periods and restrictions imposed on Restricted
    Shares shall lapse, and within ten (10) business days after the occurrence
    of a Change in Control, the stock certificates representing Shares of
    Restricted Stock, without any restrictions or legend thereon, shall be
    delivered to the applicable Participants;
 
        (c) The target value attainable under all Performance Units and
    Performance Shares shall be deemed to have been fully earned for the entire
    Performance Period as of the effective date of the Change in Control, and
    shall be paid out in cash to Participants within thirty (30) days following
    the effective date of the Change in Control; provided, however, that there
    shall not be an accelerated payout with respect to Performance Units or
    Performance Shares which were granted less than six (6) months prior to the
    effective date of the Change in Control;
 
        (d) Subject to Article 14 herein, the Committee shall have the authority
    to make any modifications to the Awards as determined by the Committee to be
    appropriate before the effective date of the Change in Control.
 
                                      A-13
<PAGE>
              ARTICLE 14. AMENDMENT, MODIFICATION, AND TERMINATION
 
    14.1  AMENDMENT, MODIFICATION AND TERMINATION.  With the approval of the
Board, at any time and from time to time, the Committee may terminate, amend or
modify the Plan.
 
    14.2  AWARDS PREVIOUSLY GRANTED.  No termination, amendment, or modification
of the Plan shall adversely affect in any material way any Award previously
granted under the Plan, without the written consent of the affected Participant
(or if the Participant is not then living, the affected beneficiary); provided
that adjustments pursuant to Section 4.3 shall not be subject to the foregoing
limitations of this Section 14.2.
 
                            ARTICLE 15. WITHHOLDING
 
    15.1  TAX WITHHOLDING.  The Company shall have the power and the right to
deduct or withhold, or require a Participant to remit to the Company, an amount
sufficient to satisfy Federal, state, and local taxes (including the
Participant's FICA obligation) required by law to be withheld with respect to
any taxable event arising or as a result of this Plan.
 
    15.2  SHARE WITHHOLDING.  With respect to withholding required upon the
exercise of Options or SARs, upon the lapse of restrictions on Restricted Stock,
or upon any other taxable event hereunder, Participants may elect, subject to
the approval of the Committee, to satisfy the withholding requirement, in whole
or in part, by having the Company withhold Shares having a Fair Market Value on
the date the tax is to be determined equal to the minimum statutory total tax
which could be imposed on the transaction. All elections shall be irrevocable,
made in writing and signed by the Participant, and elections by Insiders shall
additionally comply with any applicable requirements of Rule 16b-3 of the
Exchange Act.
 
                          ARTICLE 16. INDEMNIFICATION
 
    Each person who is or shall have been a member of the Committee, or of the
Board, shall be indemnified and held harmless by the Company against and from
any loss, cost, liability, or expense that may be imposed upon or reasonably
incurred by him or her in connection with or resulting from any claim, action,
suit, or proceeding to which he or she may be a party or in which he or she may
be involved by reason of any action taken or failure to act under the Plan and
against and from any and all amounts paid by him or her in settlement thereof,
with the Company's approval, or paid by him or her in satisfaction of any
judgment in any such action, suit, or proceeding against him or her, provided he
or she shall give the Company an opportunity, at its own expense, to handle and
defend the same before he or she undertakes to handle and defend it on his or
her own behalf. The foregoing right of indemnification shall not be exclusive of
any other rights of indemnification to which such persons may be entitled under
the Company's Articles of Incorporation or By-laws, as a matter of law, or
otherwise, or any power that the Company may have to indemnify them or hold them
harmless.
 
                             ARTICLE 17. SUCCESSORS
 
    All obligations of the Company under the Plan, with respect to Awards
granted hereunder, shall be binding on any successor to the Company, whether the
existence of such successor is the result of a direct or indirect purchase,
merger, consolidation, or otherwise, of all or substantially all of the business
and/or assets of the Company.
 
                                      A-14
<PAGE>
                         ARTICLE 18. LEGAL CONSTRUCTION
 
    18.1  GENDER AND NUMBER.  Except where otherwise indicated by the context,
any masculine term used herein also shall include the feminine; the plural shall
include the singular and the singular shall include the plural.
 
    18.2  SEVERABILITY.  In the event any provision of the Plan shall be held
illegal or invalid for any reason, the illegality or invalidity shall not affect
the remaining parts of the Plan, and the Plan shall be construed and enforced as
if the illegal or invalid provision had not been included.
 
    18.3  REQUIREMENTS OF LAW.  The granting of Awards and the issuance of
Shares under the Plan shall be subject to all applicable laws, rules, and
regulations, and to such approvals by any governmental agencies or national
securities exchanges as may be required.
 
    18.4  SECURITIES LAW COMPLIANCE.  Transactions under this Plan are intended
to comply with all applicable conditions or Rule 16b-3 or its successors under
the Exchange Act. To the extent any provision of the plan or action by the
Committee fails to so comply, it shall be deemed null and void, to the extent
permitted by law and deemed advisable by the Committee.
 
    18.5  GOVERNING LAW.  To the extent not preempted by Federal law, the Plan,
and all agreements hereunder, shall be construed in accordance with and governed
by the laws of the State of Wisconsin.
 
                                      A-15
<PAGE>
                                                                      APPENDIX B
 
                        EXECUTIVE ANNUAL INCENTIVE PLAN
 
                     AMERICAN MEDICAL SECURITY GROUP, INC.
 
                                 FEBRUARY 1999
<PAGE>
                                    CONTENTS
 
<TABLE>
<S>        <C>                                                                             <C>
Article    Purposes and Effective Date...................................................
  1.                                                                                               2
 
Article    Definitions...................................................................
  2.                                                                                               2
 
Article    Designation of Participants...................................................
  3.                                                                                               2
 
Article    Determination of Performance Goal.............................................
  4.                                                                                               3
 
Article    Determination of Awards for Eligible Employees................................
  5.                                                                                               4
 
Article    Payment and Deferral..........................................................
  6.                                                                                               4
 
Article    Other Provisions..............................................................
  7.                                                                                               4
</TABLE>
 
                                      B-1
<PAGE>
                     AMERICAN MEDICAL SECURITY GROUP, INC.
                        EXECUTIVE ANNUAL INCENTIVE PLAN
 
ARTICLE 1. PURPOSES AND EFFECTIVE DATE
 
    The purpose of the Executive Annual Incentive Plan is to encourage superior
performance by executives of American Medical Security Group, Inc. and its
subsidiaries (collectively, the "Company") through the payment of annual cash
incentive awards. This Plan is also intended to exempt annual incentive payments
to Covered Employees (as defined in Article 2, below) as performance-based
compensation from the $1 million cap on deductible pay, as set forth in Section
162(m) of the Internal Revenue Code and the Plan shall be construed and
administered accordingly.
 
    This Plan is effective as of January 1, 1999.
 
ARTICLE 2. DEFINITIONS
 
2.1
 
    The following items shall have the meanings set forth below, if capitalized.
 
    (a) "Board" shall mean the Board of Directors of the Company.
 
    (b) "CEO" means the Chief Executive Officer of the Company.
 
    (c) "Committee" means the Compensation Committee of the Board of Directors
of American Medical Security Group, Inc.
 
    (d) "Covered Employee" means a Participant designated prior to the grant of
an award by the Committee who is or may be a "covered employee" within the
meaning of Section 162(m)(3) of the Internal Revenue Code in the year in which
such award is taxable to the Participant.
 
    (e) "Eligible Employee" shall mean key employees of the Company who, in the
opinion of the Committee, are or give promise of becoming of exceptional
importance to the Company and of making substantial contributions to the
success, growth, and profit of the Company.
 
    (f) "Participant" means an employee deemed to be an Eligible Employee for a
Plan Year.
 
    (g) "Plan" means the American Medical Security Group, Inc. Executive Annual
Incentive Plan as it may be amended from time to time.
 
    (h) "Plan Year" means the calendar year.
 
    (i) "Retirement" means early, normal or postponed retirement as defined
under the retirement policy of the Company.
 
ARTICLE 3. DESIGNATION OF PARTICIPANTS
 
3.1
 
    Awards may be made only to Eligible Employees.
 
3.2
 
    No member of the Committee, and no member of the Board of Directors of the
Company who is not also a regular salaried employee of the Company, shall be
eligible to participate in the Plan
 
                                      B-2
<PAGE>
3.3
 
    The Committee may, but need not, consider for prorated or full incentive
awards Participants who have ceased employment because of death, disability, or
Retirement prior to the date the Committee determines incentive awards under the
Plan. Participants who terminate employment (or give notice of intent to
terminate employment) for reasons other than death, disability, or Retirement
prior to the date the Committee determines the incentive awards under the Plan
will not be eligible to be considered for an incentive award, unless the
Committee determines in its sole discretion that, because of special
circumstances, the Participant shall be eligible to be considered.
 
3.4
 
    Participation in the Plan shall not entitle any Eligible Employee to an
award under the Plan. All awards shall be made in the sole discretion of the
Committee.
 
ARTICLE 4. DETERMINATION OF PERFORMANCE GOALS
 
4.1
 
    The terms and conditions of any award that is intended to provide
performance-based compensation to a Covered Employee shall include the
requirement that such award shall be payable only on account of the attainment
of one or more preestablished performance goals determined by the Committee. The
agreement covering such award shall specify the performance goals to which
payment under the award is subject and shall state, in terms of an objective
formula or standard, the method for computing the amount of compensation payable
to the Participant if the goal is obtained. In addition, before the payment of
any such award, the Committee shall certify that the performance goals and any
other material terms of the award have in fact been satisfied.
 
4.2
 
    For purposes of the foregoing, the Committee shall specify the performance
goals and certify the attainment of such goals with respect to
performance-related awards in accordance with Code Section 162(m) and related
rules and regulations followed by the Internal Revenue Service. Except as
otherwise permitted or required by such authorities, the performance goals
applicable to each award subject to this paragraph shall be determined by the
Committee in a manner such that any compensation of a Participant under the
award is paid pursuant to a preestablished objective performance formula or
standard that precludes discretion and generally allows a third party with
knowledge of the relevant performance results to calculate the amount to be paid
to the Participant.
 
4.3
 
    In general, the reservation of a right to reduce or eliminate the
compensation or other economic benefit that was due on attainment of the
performance goal shall not be considered to be impermissible discretion under
Section 162(m) of the Internal Revenue Code, nor shall the choice to pay upon
the attainment of either of two objective preestablished performance goals. The
Committee reserves such right and the ability to make such choice. A
performance-based compensation award applicable to a Covered Employee may be
based on the attainment of goals relating to one or more of the following
business criteria, measured on an absolute basis or in terms of growth or
reduction: net income (pre-tax or after-tax and with adjustments as stipulated),
earnings per share, return on equity, return on assets, return on tangible book
value, operating income, earnings before depreciation, interest, taxes and
amortization (EBDITA), loss ratio, expense ratio, increase in stock price, total
shareholder return, economic value added, and operating cash flow. With respect
to Participants who are not Covered Employees, the
 
                                      B-3
<PAGE>
Committee may establish other subjective or objective performance goals,
including individual goals, which it deems appropriate.
 
ARTICLE 5. DETERMINATION OF AWARDS FOR ELIGIBLE EMPLOYEES
 
5.1
 
    The CEO shall recommend to the Committee target award levels for each
Eligible Employee who is a Participant as soon as practicable after the
beginning of the Plan Year.
 
5.2
 
    After the end of the Plan Year, each Participant's performance shall be
assessed by the Committee pursuant to the applicable preestablished performance
goals for such Plan Year.
 
5.3
 
    The designation of annual award recipients and the amount of individual
awards shall be determined by the Committee pursuant to the applicable
preestablished performance goals and such other rules as the Committee may
establish. However, in no event may any Participant's annual incentive award
exceed $3,000,000.
 
ARTICLE 6. PAYMENT AND DEFERRAL
 
6.1
 
    Incentive awards granted by the Committee, less applicable withholding
taxes, shall be paid in cash as soon as reasonably possible after being awarded.
 
6.2
 
    The Committee may permit or require a Participant to defer such
Participant's receipt of the payment of cash that would otherwise be due to such
Participant. If any such deferral election is required or permitted, the
Committee shall, in is sole discretion, establish rules and procedures for such
payment deferrals.
 
ARTICLE 7. OTHER PROVISIONS
 
7.1
 
    The Board of Directors of American Medical Security Group, Inc. reserves the
right to modify, suspend or terminate this Plan at any time.
 
7.2
 
    The Committee shall have the power to construe and interpret the Plan and to
establish rules not inconsistent with the provisions of the Plan. Any decision
arising out of or in connection with the construction, interpretation and
administration of the Plan shall lie within the Committee's absolute discretion
and shall be binding on all parties.
 
7.3
 
    The designation of an employee as a Participant or the grant of an award to
an employee shall not give such employee any right to be retained in the employ
of the Company and the ability of the Company to dismiss or discharge the
employee is specifically reserved.
 
                                      B-4
<PAGE>
7.4
 
    No Participant shall have the right to alienate, assign, encumber,
hypothecate or pledge his or her interest in any award under the Plan,
voluntarily or involuntarily, prior to payment and any attempt to dispose of any
such interest shall be void. Notwithstanding the preceding sentence, the Company
shall have the right to offset from an unpaid or deferred award any amounts due
and owing from the Participant to the extent permitted by law. The Company shall
not be required to segregate physically any cash or to establish any separate
account or accounts to fund any awards made or to be made under the Plan.
 
7.5
 
    This document is a complete statement of the Plan and as of the effective
date supersedes all prior plans, proposals, representations, promises and
inducements, written or oral, relating to its subject matter. The Company shall
not be bound by or liable to any person for any representation, promise or
inducement made by any person which is not embodied in this document or in any
authorized written amendment to the Plan
 
7.6
 
    The Plan shall be construed and enforced in accordance with Wisconsin law
without regard to principles of conflicts of law.
 
                                      B-5
<PAGE>


                     AMERICAN MEDICAL SECURITY GROUP, INC.

                         ANNUAL MEETING OF SHAREHOLDERS
                                 MAY 27, 1999

          THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS


SAMUEL V. MILLER, EDWARD R. SKOLDBERG AND GARY D. GUENGERICH, and each of 
them, are hereby authorized as Proxies, with full power of substitution, to 
represent and vote the Common Stock of the Undersigned at the Annual Meeting 
of Shareholders of American Medical Security Group, Inc., a Wisconsin 
corporation, to be held on Thursday, May 27, 1999, or any adjournment or 
postponement thereof, with like effect as if the undersigned were personally 
present and voting, upon the matters indicated on the reverse side of this 
card:


THIS PROXY WHEN PROPERLY EXECUTED WILL BE VOTED IN THE MANNER SPECIFIED 
HEREIN BY THE UNDERSIGNED SHAREHOLDER. IF NO SPECIFICATION IS MADE, THIS 
PROXY WILL BE VOTED FOR PROPOSALS 1, 2 AND 3.


(SEE REVERSIDE SIDE TO VOTE)


<PAGE>


                     AMERICAN MEDICAL SECURITY GROUP, INC.

                         ANNUAL MEETING OF SHAREHOLDERS
                                 MAY 27, 1999









                                (SEE REVERSE SIDE)

    PLEASE SIGN, DATE, DETACH BELOW AND RETURN USING THE ENVELOPE PROVIDED
                                 PLEASE DO NOT FOLD



         AMERICAN MEDICAL SECURITY GROUP, INC. 1999 ANNUAL MEETING


1. ELECTION OF DIRECTORS: 

   1 - ROGER H. BALLOU       / /  FOR all nominees       / /  WITHHOLD AUTHORITY
   2 - W. FRANCIS BRENNAN         listed to the left          to vote for all
   3 - J. GUS SWOBODA             (except as specified        nominees listed to
                                  below).                     the left.

(Instructions: To withhold authority to vote for any indicated nominee,
write the number(s) of the nominee(s) in the box provided to the right).  /  /


2. To amend the American Medical Security 
   Group, Inc. Equity Incentive Plan:         / / FOR  / / AGAINST  / / ABSTAIN


3. To approve the American Medical Security
   Group Inc. Executive Annual Incentive 
   Plan:                                      / / FOR  / / AGAINST  / / ABSTAIN


4. In their discretion, upon such other business as may properly come before 
   the Meeting or any adjournments thereof; 

   all as set out in the Notice and Proxy Statement relating to the Meeting, 
   receipt of which is hereby acknowledged.

Check appropriate box          Date _______________          NO. OF SHARES
Indicate changes below:
Address Change?             / / Name Change?  / /



                                           ________________________________
                                           SIGNATURE(S) IN BOX
                                           PLEASE SIGN PERSONALLY AS NAME
                                           APPEARS AT LEFT.  When signing as
                                           attorney, executor, administrator,
                                           personal representative, trustee or
                                           guardian, please give full title as
                                           such. If signer is a corporation, 
                                           sign full corporate name by duly
                                           authorized officer. If stock is held
                                           in the name of two or more persons,
                                           all should sign.



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