DIGITAL ISLAND INC
424B3, 2000-08-10
BUSINESS SERVICES, NEC
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<PAGE>

                                                Filed Pursuant to Rule 424(b)(3)
                                                           File Number 333-41540


                               1,012,642 Shares

                             DIGITAL ISLAND, INC.
                                 Common Stock



     This prospectus relates to the public offering, which is not being
underwritten, of 1,012,642 shares of our Common Stock, which are held by
some of our current stockholders.

     The prices at which such stockholders may sell the shares will be
determined by the prevailing market price for the shares or in negotiated
transactions. We will not receive any of the proceeds from the sale of the
shares.

     Our Common Stock is quoted on the Nasdaq National Market under the symbol
"ISLD." On July 11, 2000, the average of the high and low price for the
Common Stock was $40.00.

     INVESTING IN OUR COMMON STOCK INVOLVES RISKS. SEE THE SECTIONS ENTITLED
"RISK FACTORS" IN THE DOCUMENTS WE FILED WITH THE SECURITIES AND EXCHANGE
COMMISSION THAT ARE INCORPORATED BY REFERENCE IN THIS PROSPECTUS FOR CERTAIN
RISKS AND UNCERTAINTIES THAT YOU SHOULD CONSIDER.


                        -------------------------------

     Neither the Securities and Exchange Commission nor any state securities
commission has approved or disapproved of these securities or passed upon the
adequacy or accuracy of this prospectus. Any representation to the contrary is a
criminal offense.

                        -------------------------------





================================================================================

                 The date of this prospectus is August 10, 2000
<PAGE>

          No person has been authorized to give any information or to make any
representations other than those contained in this prospectus in connection with
the offering made hereby, and if given or made, such information or
representations must not be relied upon as having been authorized by Digital
Island, Inc. (referred to in this prospectus as "Digital Island" or the
"Registrant"), any Selling Stockholder (as defined below) or by any other
person. Neither the delivery of this prospectus nor any sale made hereunder
shall, under any circumstances, create any implication that information herein
is correct as of any time subsequent to the date hereof. This prospectus does
not constitute an offer to sell or a solicitation of an offer to buy any
security other than the securities covered by this prospectus, nor does it
constitute an offer to or solicitation of any person in any jurisdiction in
which such offer or solicitation may not lawfully be made.

                             AVAILABLE INFORMATION

          Digital Island is subject to the informational requirements of the
Securities Exchange Act of 1934, as amended (the "Exchange Act"), and in
accordance therewith files reports, proxy statements, information statements and
other information with the Securities and Exchange Commission (the "SEC"). You
may read and copy any document that we file at the SEC's Public Reference Room
at 450 Fifth Street, N.W., Washington, D.C. 20549. Please call the SEC at 1-800-
SEC-0330 for further information on the operation of the Public Reference Room.
Our SEC filings are also available to the public from the SEC's web site at
http://www.sec.gov

          Digital Island has filed with the Commission a registration statement
on Form S-3 (herein, together with all amendments and exhibits thereto, referred
to as the "Registration Statement") under the Securities Act of 1933, as amended
(the "Securities Act") with respect to the Common Stock offered hereby. This
prospectus does not contain all of the information set forth in the Registration
Statement, certain parts of which are omitted in accordance with the rules and
regulations of the Commission.

          The SEC allows us to "incorporate by reference" the information we
file with them, which means that we can disclose important information to you by
referring to those documents. The information incorporated by reference is
considered to be part of the prospectus, and later information filed with the
SEC will update and supersede this information. We incorporate by reference the
documents listed below and any future filings made with the SEC under Section
13a, 13(c), 14, or 15(d) of the Exchange Act until our offering is completed.

                INCORPORATION OF CERTAIN DOCUMENTS BY REFERENCE

          The following documents filed with the Commission (File No. 1-11921)
pursuant to the Exchange Act are incorporated herein by reference:

          1.   Digital Island's Annual Report on Form 10-K for the year ended
September 30, 1999, filed on December 28, 1999;

          2.   Digital Island's Quarterly Report on Form 10-Q for the quarter
ended December 31, 1999, filed on February 11, 2000 (as amended by Form 10-Q/A
as filed on February 22, 2000);

          3.   Definitive Proxy Statement, dated March 21, 2000, filed on March
21, 2000 in connection with Digital Island's 2000 Annual Meeting of
Stockholders;

          4.   Digital Island's Quarterly Report on Form 10-Q for the quarter
ended March 31, 2000, filed on May 15, 2000;

          5.   The description of Digital Island's Common Stock, $0.001 par
value per share, and associated rights, contained in its registration statement
on Form 8-A, filed on June 7, 1999, including any amendment or report filed for
the purpose of updating such description;

          6.   Digital Island's Current Report on Form 8-K filed October 27,
1999;

          7.   Digital Island's Current Report on Form 8-K filed on December 9,
1999;

          8.   Digital Island's Current Report on Form 8-K filed on January 5,
2000;

          9.   Digital Island's Current Report on Form 8-K filed on July 6,
2000;

         10.   Digital Island's Current Report on Form 8-K filed on July 17,
2000; and

                                       1
<PAGE>

          11.  All reports and other documents filed by Digital Island pursuant
to Sections 13(a), 13(c), 14 or 15(d) of the Exchange Act subsequent to the date
of this prospectus and prior to the termination of the offering.

          Any statement contained in a document incorporated by reference herein
shall be deemed to be incorporated by reference in this prospectus and to be
part hereof from the date of filing of such documents. Any statement modified or
superseded shall not be deemed, except as so modified or superseded, to
constitute a part of this prospectus. You should not assume that the information
in this prospectus or any prospectus supplement is accurate as of any date other
than the date on the front of the document. Digital Island will provide without
charge to each person to whom this prospectus is delivered a copy of any or all
of such documents which are incorporated herein by reference (other than
exhibits to such documents unless such exhibits are specifically incorporated by
reference into the documents that this prospectus incorporates). Written
requests for copies should be directed to Digital Island, Inc., Investor
Relations, 45 Fremont Street, 12th Floor, San Francisco, California 94105.
Digital Island's telephone number is (650) 738-4100.

                                  THE COMPANY

          The principal executive offices of Digital Island are located at 45
Fremont Street, 12th Floor, San Francisco, California 94105. Digital Island's
telephone number is (415) 738-4100.

                             PLAN OF DISTRIBUTION

          Digital Island, Inc. is registering 1,012,642 shares of Common Stock,
par value of $0.001 per share, on behalf of certain selling stockholders.
Digital Island will receive no proceeds from this offering. The Shares (as
defined below) may be offered by certain stockholders of Digital Island or by
pledgees, donees, transferees or other successors in interest that receive such
Shares as a gift, partnership distribution or other non-sale related transfer
(the "Selling Stockholders"). 799,989 of the Shares (the "LOL Shares") were
originally issued by Digital Island in connection with the merger of Live On
Line, Inc. ("LOL"), a New York corporation, with LOL Acquisition, Corp. ("LOL
Acquisition"), a wholly-owned subsidiary of Digital Island, with LOL being the
surviving corporation (the "Merger"). The LOL Shares are being registered by
Digital Island pursuant to the Agreement and Plan of Merger, dated as of January
18, 2000, by and among the Digital Island, LOL Acquisition, LOL and certain of
the stockholders of LOL (the "Agreement and Plan of Merger"). The remaining
212,653 Shares (the "SRI Shares", and together with the LOL Shares, the
"Shares") were originally issued by Digital Island in connection with the
Technology Purchase Agreement and Research Alliance between SRI International, a
California nonprofit public benefit corporation and Digital Island (the
"Technology Purchase Agreement"). The SRI Shares are being registered by Digital
Island pursuant to the Registration Rights Agreement, dated as of July 1, 2000,
by and between Digital Island and SRI (the "Rights Agreement"). The Shares were
issued pursuant to exemptions from the registration requirements of the
Securities Act of 1933, as amended (the "Securities Act"), provided by Section
4(2) thereof.

          The Selling Stockholders will act independently of Digital Island in
making decisions with respect to the timing, manner and size of each sale. The
sales may be made on one or more exchanges or in the over-the-counter market or
otherwise, at prices and at terms then prevailing or at prices related to the
then current market price, or in negotiated transactions. The Selling
Stockholders may effect such transactions by selling the Shares to or through
broker-dealers. The Shares may be sold by one or more, or a combination of, the
following: (a) a block trade in which the broker-dealer so engaged will attempt
to sell the Shares as agent but may position and resell a portion of the block
as principal to facilitate the transaction; (b) purchases by a broker-dealer as
principal and resale by such broker-dealer for its account pursuant to this
prospectus; (c) an exchange distribution in accordance with the rules of such
exchange; (d) ordinary brokerage transactions and transactions in which the
broker solicits purchasers and (e) in privately negotiated transactions. To the
extent required, this prospectus may be amended or supplemented from time to
time to describe a specific plan of distribution. In effecting sales, broker-
dealers engaged by the Selling Stockholders may arrange for other broker-dealers
to participate in the resales.

          In connection with distributions of the Shares or otherwise, the
Selling Stockholders may enter into hedging transactions with broker-dealers. In
connection with such transactions, broker-dealers may engage in short sales of
the Shares in the course of hedging the positions they assume with Selling
Stockholders. The Selling Stockholders may also sell Shares short and redeliver
the Shares to close out such short positions. The Selling Stockholders may also
enter into option or other transactions with broker-dealers which require the
delivery to the broker-dealer of the Shares registered hereunder, which the
broker-dealer may resell or otherwise transfer pursuant to this prospectus. The
Selling Stockholder may also loan or pledge the Shares registered hereunder to a
broker-dealer and the broker-dealer may sell the Shares so loaned or upon a
default the broker-dealer may effect sales of the pledged shares pursuant to
this prospectus.

          Broker-dealers or agents may receive compensation in the form of
commissions, discounts or concessions from Selling Stockholders and/or the
purchasers of the Shares for whom such broker-dealers may act as agents or to
whom they sell as principals, or both (which compensation as to a particular
broker-dealer might be in excess of customary commissions) in amounts to be
negotiated in connection with the sale. Such broker-dealers or agents and any
other participating broker-dealers or the Selling Stockholders may be deemed to
be "underwriters" within the meaning of Section 2(11) of the Securities Act in
connection with such sales and any such commission, discount or concession may
be deemed to be underwriting discounts or commissions under the Securities Act.
Because the Selling Stockholder may be deemed to be an underwriter within the
meaning of Section 2(11) of the Securities Act, the Selling Stockholders will be
subject to the prospectus delivery requirements of the Securities Act. In
addition, any securities covered by this prospectus which qualify for sale
pursuant to Rule 144 may be sold under Rule 144 rather than pursuant to this
prospectus. The Selling Stockholders have advised Digital Island that they

                                       2
<PAGE>

have not entered into any agreements, understandings or arrangements with any
underwriters or broker-dealers regarding the sale of their securities. There is
no underwriter or coordinating broker acting in connection with the proposed
sale of the Shares by Selling Stockholders.

          In order to comply with the securities laws of certain states, if
applicable, the Shares will be sold in such jurisdictions only through
registered or licensed brokers or dealers. In addition, in certain states the
Shares may not be sold unless they have been registered or qualified for sale in
the applicable state or an exemption from the registration or qualification
requirement is available and is complied with.

          Under applicable rules and regulations under the Exchange Act, any
person engaged in the distribution of the Shares may not simultaneously engage
in market making activities with respect to our common stock for a period of two
business days prior to the commencement of such distribution. In addition and
without limiting the foregoing, each Selling Stockholder will be subject to
applicable provisions of the Exchange Act and the associated rules and
regulations thereunder, including, without limitation, Regulation M, which
provisions may limit the timing of purchases and sales of shares of our common
stock by the Selling Stockholders. Digital Island will make copies of this
prospectus available to the Selling Stockholders and has informed them of the
need for delivery of copies of this prospectus to purchasers at or prior to the
time of any sale of the Shares offered hereby. Digital Island assumes no
obligation to so deliver copies of this prospectus or any related prospectus
supplement.

          Digital Island will file a supplement to this prospectus, if required,
pursuant to Rule 424(b) under the Securities Act upon being notified by a
Selling Stockholder that any material arrangement has been entered into with a
broker-dealer for the sale of shares through a block trade, special offering,
exchange distribution or secondary distribution or a purchase by a broker or
dealer. Such supplement will disclose: (a) the name of each such Selling
Stockholder and of the participating broker-dealer(s), (b) the number of shares
involved, (c) the price at which such shares were sold, (d) the commissions paid
or discounts or concessions allowed to such broker-dealer(s), where applicable,
(e) that such broker-dealer(s) did not conduct any investigation to verify the
information set out or incorporated by reference in this prospectus and (f)
other facts material to the transaction.

          The Selling Stockholders will be responsible for any fees,
disbursements and expenses of any counsel for the Selling Stockholders. All
other expenses incurred in connection with the registration of the Shares,
including printer's and accounting fees and the fees, disbursements and expenses
of counsel for Digital Island will be borne by us. Commissions and discounts, if
any, attributable to the sales of the Shares will be borne by the Selling
Stockholders. The Selling Stockholders may agree to indemnify any broker-dealer
or agent that participates in transactions involving sales of the Shares against
certain liabilities, including liabilities arising under the Securities Act.
Digital Island will indemnify the Selling Stockholders against claims arising
out of any untrue statement of a material fact contained in this Registration
Statement or any omission to state therein a material fact necessary in order to
make the statement made therein not misleading.

          Digital Island has undertaken to keep a Registration Statement of
which this prospectus constitutes a part effective until the earlier of the
disposition of the securities offered hereby or January 18, 2001. After such
period, if we choose not to maintain the effectiveness of the registration
statement of which this prospectus constitutes a part, the securities issuable
offered hereby may not be sold, pledged, transferred or assigned, except in a
transaction which is exempt under the provisions of the Securities Act or
pursuant to an effective registration statement thereunder.

                                       3
<PAGE>

                             SELLING STOCKHOLDERS

          The following table sets forth the number of shares of common stock
owned by each of the Selling Stockholders and the percentage of the total
outstanding shares of Digital Island owned by each Selling Stockholder as of
June 30, 2000. None of the Selling Stockholders has had a material
relationship with Digital Island within the past three years other than as a
result of the ownership of the Shares or other securities of Digital Island or
as a result of their employment with Digital Island as of the date of the
closing of the acquisition. Because the Selling Stockholders may offer all or
some of the Shares which they hold pursuant to the offering contemplated by
this prospectus, and because there are currently no agreements, arrangements
or understandings with respect to the sale of any of the Shares, no estimate
can be given as to the amount of the Shares that will be held by the Selling
Stockholders after completion of this offering. No Selling Stockholder
beneficially owns 1% or more of the outstanding shares of common stock of
Digital Island. The Shares offered by this prospectus may be offered from time
to time by the Selling Stockholders named below.

<TABLE>
<CAPTION>
                                                                                                   Number of Shares
                                                   Number of Shares             Percent of       Registered for Sale
     Name of Selling Stockholder                  Beneficially Owned        Outstanding Shares        Hereby (1)
     ---------------------------                  ------------------        ------------------   --------------------
<S>                                              <C>                        <C>                  <C>
Adam Cohen                                                295,340                    *                 295,340

Michael Fiorentino                                          7,731                    *                   7,731

Debra LaChance                                            310,030                    *                 310,030

Alan G. Schatten                                           42,522                    *                  42,522

Victor Starsia                                             77,314                    *                  77,314

Jennifer Sultan                                            40,203                    *                  40,203

SRI International                                         212,653                    *                 212,653

Veronis, Suhler & Associates, Inc.                         25,053                    *                  25,053

Beverly Westle                                              1,796                    *                   1,796
                                                  -------------------------------------------------------------------
TOTAL                                                   1,012,642                  1.5%              1,012,642
--------------
</TABLE>

*    Represents beneficial ownership of less than one percent.

(1)  This Registration Statement shall also cover any additional shares of
common stock which become issuable in connection with the shares registered for
sale hereby by reason of any stock dividend, stock split, recapitalization or
other similar transaction effected without the receipt of consideration which
results in an increase in the number of the Digital Island's outstanding shares
of common stock.

                                       4
<PAGE>

                                 LEGAL MATTERS

          The validity of the securities offered hereby will be passed upon for
Digital Island by Brobeck, Phleger & Harrison LLP, Palo Alto, California.

                                    EXPERTS

          The consolidated financial statements of Digital Island, Inc. and its
subsidiaries, incorporated in this prospectus by reference to Digital Island,
Inc.'s Annual Report on Form 10-K for the year ended September 30, 1999, have
been incorporated in reliance upon the report of PricewaterhouseCoopers LLP,
independent accountants, given on the authority of said firm as experts in
accounting and auditing.


          The consolidated financial statements of Sandpiper Networks, Inc. at
December 31, 1998 and 1997, and for each of the two years in the period ended
December 31, 1998, incorporated by reference in this Prospectus and
Registration Statement have been audited by Ernst & Young LLP, independent
auditors, as set forth in their report thereon, and are incorporated by
reference in reliance upon such report given on the authority of such firm as
experts in accounting and auditing.

                                       5
<PAGE>

          We have not authorized any person to make a statement that differs
from what is in this prospectus. If any person does make a statement that
differs from what is in this prospectus, you should not rely on it. This
prospectus is not an offer to sell, nor is it seeking an offer to buy, these
securities in any state in which the offer or sale is not permitted. The
information in this prospectus is complete and accurate as of its date, but the
information may change after that date.


                           -------------------------

                               TABLE OF CONTENTS


<TABLE>
<CAPTION>
                                                                     Page
                                                                     ----
      <S>                                                            <C>
      Available Information........................................    1
      Incorporation of Certain Documents by Reference..............    1
      The Company..................................................    2
      Plan of Distribution.........................................    2
      Selling Stockholders.........................................    4
      Legal Matters................................................    5
      Experts......................................................    5
</TABLE>



                            DIGITAL ISLAND, INC.

                              1,012,642 Shares
                               of Common Stock

          ---------------------------------------------------------


                                 Prospectus


          ---------------------------------------------------------


                                August 10, 2000


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