WORLDTALK COMMUNICATIONS CORP
S-3, 1999-09-08
PREPACKAGED SOFTWARE
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    As filed with the Securities and Exchange Commission on September 8, 1999
                                             Registration No. 333-______________

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

                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549

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

                                    FORM S-3
                             REGISTRATION STATEMENT
                                      Under
                           THE SECURITIES ACT OF 1933

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

                      WORLDTALK COMMUNICATIONS CORPORATION
             (Exact name of Registrant as specified in its charter)

            Delaware                                              77-0303581
(State or other jurisdiction of                               (I.R.S. employer
  incorporation or organization)                             identification no.)

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

                            5155 Old Ironsides Drive
                          Santa Clara, California 95054
                                 (408) 567-1500
               (Address, including zip code, and telephone number,
        including area code, of Registrant's principal executive offices)

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

                                  James Heisch
                             Chief Financial Officer
                      Worldtalk Communications Corporation
                            5155 Old Ironsides Drive
                          Santa Clara, California 95054
                                 (408) 567-1500
            (Name, address, including zip code, and telephone number,
                   including area code, of agent for service)

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

                                   Copies to:

                              Gail E. Suniga, Esq.
                             Tyler R. Cozzens, Esq.
                            Pamela A. Sergeeff, Esq.
                               Fenwick & West LLP
                              Two Palo Alto Square
                           Palo Alto, California 94306

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

  Approximate date of commencement of proposed sale to the public: From time to
   time after the effective date of this Registration Statement until July 7,
       2001 or until the earlier sale of all shares registered hereunder.

         If the only securities  being registered on this Form are being offered
pursuant to dividend or interest  reinvestment plans, please check the following
box. |_|

         If any of the  securities  being  registered  on  this  Form  are to be
offered  on a  delayed  or  continuous  basis  pursuant  to Rule 415  under  the
Securities Act of 1933,  other than  securities  offered only in connection with
dividend or interest reinvestment plans, check the following box. |X|

         If this Form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, please check the following box
and list  the  Securities  Act  registration  statement  number  of the  earlier
effective registration statement for the same offering. |_| _____________

         If this  Form is a  post-effective  amendment  filed  pursuant  to Rule
462(c) under the Securities Act, check the following box and list the Securities
Act  registration   statement  number  of  the  earlier  effective  registration
statement for the same offering. |_|_____________

         If delivery of the  prospectus  is expected to be made pursuant to Rule
434, please check the following box. |_|


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

<TABLE>
                                                   CALCULATION OF REGISTRATION FEE
<CAPTION>
- ------------------------------------------------------------------------------------------------------------------------------------
                                                               Proposed Maximum           Proposed Maximum
  Title of Each Class of Securities       Amount to be        Offering Price per         Aggregate Offering          Amount of
           to be Registered              Registered (1)            Share(2)                   Price(2)           Registration  Fee
- ------------------------------------------------------------------------------------------------------------------------------------
<S>                                     <C>                        <C>                      <C>                    <C>
Common Stock, par value $0.01 per
share                                   5,720,735 shares           $3.61                    $20,651,854            $5,742
- ------------------------------------------------------------------------------------------------------------------------------------

<FN>
(1)  The  shares of  common  stock  set  forth in this  table,  and which may be
     offered pursuant to this Registration Statement, includes, pursuant to Rule
     416 under the Securities Act of 1933, as amended, such additional number of
     shares of common  stock that may become  issuable  as a result of any stock
     splits, stock dividends or similar events.

(2)  Estimated  solely  for  the  purpose  of  calculating  the  amount  of  the
     registration fee, pursuant to Rule 457(c) under the Securities Act of 1933,
     as  amended,  based on the average of the high and low prices of the common
     stock on the Nasdaq National Market on September 1, 1999.
</FN>
</TABLE>

         The Registrant hereby amends this  Registration  Statement on such date
or dates as may be necessary to delay its  effective  date until the  Registrant
shall file a further amendment which specifically  states that this Registration
Statement shall  thereafter  become effective in accordance with Section 8(a) of
the Securities  Act of 1933 or until this  Registration  Statement  shall become
effective on such date as the Commission,  acting pursuant to said Section 8(a),
may determine.

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


<PAGE>


THE INFORMATION CONTAINED IN THIS PROSPECTUS IS NOT COMPLETE AND MAY BE CHANGED.
WE MAY NOT SELL THESE SECURITIES UNTIL THE REGISTRATION STATEMENT FILED WITH THE
SECURITIES AND EXCHANGE COMMISSION IS EFFECTIVE. THIS PROSPECTUS IS NOT AN OFFER
TO  SELL  THESE  SECURITIES  AND IT IS NOT  SOLICITING  AN  OFFER  TO BUY  THESE
SECURITIES IN ANY STATE WHERE THE OFFER OR SALE IS NOT PERMITTED.


               SUBJECT TO COMPLETION, DATED SEPTEMBER 8, 1999

PROSPECTUS


                                5,720,735 SHARES

                      WORLDTALK COMMUNICATIONS CORPORATION

                                  COMMON STOCK

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

         The selling  stockholders  identified on page 14 of this prospectus are
offering these shares of common stock. For additional information on the methods
of sale, you should refer to the section entitled "Plan of Distribution" on page
15. We will not receive any proceeds from the sale of these shares.

         The common  stock is listed on the  Nasdaq  National  Market  under the
symbol "WTLK."

         On September 7, 1999, the last sale price of the common stock on the
Nasdaq National Market was $3.625 per share.


   Investing in the common stock involves risks. See "Risk Factors" on page 4.



         Neither the Securities and Exchange Commission nor any state securities
commission has approved or disapproved of these securities or determined if this
prospectus  is truthful or  complete.  Any  representation  to the contrary is a
criminal offense.


             The date of this prospectus is ________________, 1999.

                                      -1-

<PAGE>


                                TABLE OF CONTENTS



             Worldtalk Communications Corporation................. 3

             Risk Factors......................................... 4

             Forward-Looking Statements.......................... 13

             Use of Proceeds..................................... 13

             Selling Stockholders................................ 14

             Plan of Distribution................................ 15

             Legal Matters....................................... 17

             Experts............................................. 17

             Change in Management................................ 17

             Documents Incorporated By Reference
             In This Prospectus.................................. 17

             Where You Can Find More Information................. 18

                                      -2-

<PAGE>


                      WORLDTALK COMMUNICATIONS CORPORATION

         Worldtalk Communications  Corporation is a leading provider of Internet
content  security  and  policy  management  solutions.  Our  WorldSecure  policy
management  platform enables  organizations to define and manage electronic mail
and Web security and usage policies,  reducing the risks,  costs and liabilities
associated  with  Internet  communications.  We delivered the  industry's  first
solution for managing and enforcing e-mail security  policies in September 1997.
Since  then,   organizations  have  deployed  WorldSecure  solutions  to  ensure
confidentiality  of their external  electronic mail  communications,  to protect
their  intellectual  property and to prevent unwanted  electronic mail messages,
sometimes  called spam, and viruses from entering their  computer  systems.  Our
products include WorldSecure Server,  also known as  WorldSecure/Mail,  software
that provides Windows NT-based  electronic mail firewall and policy  management,
WorldSecure Web, a Windows NT-based content security product, WorldSecure/ESP, a
surveillance program for Internet electronic mail, WorldSecure Client, a desktop
electronic mail encryption  product and NetTalk,  a Windows NT-based  electronic
mail and directory solution.

         We were incorporated in California in February 1992 and  reincorporated
in Delaware in March 1996. Our principal  executive  offices are located at 5155
Old Ironsides  Drive,  Santa Clara,  California,  95054. Our telephone number at
this   location   is   (408)   567-1500.    Our   web   site   is   located   at
http://www.worldtalk.com.  Information  contained in our web site is not part of
this prospectus.

         Worldtalk, WorldSecure, NetTalk and our company logo are our registered
trademarks. This prospectus also contains trademarks of other companies.

                                      -3-

<PAGE>


                                  RISK FACTORS

         This  offering and an  investment  in our common  stock  involve a high
degree of risk. You should carefully consider the following risk factors and the
other  information in this prospectus  before investing in our common stock. Our
business and operating results could be seriously harmed by any of the following
risks.  The trading  price of our common stock could decline due to any of these
risks, and you may lose all or part of your investment.

Our quarterly  operating  results are volatile and  difficult to predict.  If we
fail to meet the expectations of public market analysts or investors, the market
price of our common stock may decrease.

         Our  quarterly  operating  results have varied  greatly in the past and
will likely vary greatly in the future depending upon a number of factors.  Many
of these  factors are beyond our control.  Period to period  comparisons  of our
operating  results  are not  indicators  of future  performance.  Our  operating
results may fall below the  expectations of securities  analysts or investors in
some future quarter or quarters.  Our failure to meet these  expectations  would
likely cause the market price of our common stock to decline.

         Our  quarterly  operating  results  may  fluctuate  significantly  from
quarter to quarter due to, among other things:

         -   volume,  size and timing of new  licenses  and renewals of existing
             licenses;

         -   our distributor inventory levels;

         -   our  ability  to  identify,  engage  and  retain  resellers  of our
             products;

         -   introduction of new products,  product upgrades or updates by us or
             our competitors;

         -   the mix of products we sell;

         -   the success of our WorldSecure products;

         -   our  continued  evolution  as  a  provider  of  policy  enforcement
             software and the related impact on the length of our sales cycle;

         -   changes in product  prices by us or our  competitors  or changes in
             the way we set product prices;

         -   trends in the computer industry;

         -   delays or  reductions  in customer  software  purchases  related to
             their Year 2000 compliance issues;

         -   costs related to acquisitions of technology or businesses; and

         -   costs related to extraordinary events including litigation.

         Our  business  may also be affected  by  seasonal  trends and global or
regional economic trends. For example,  many companies in our industry recognize
higher revenues in the fourth quarter of each year, as customers complete annual
budgetary  cycles,  and lower revenues in the summer months when many businesses
experience lower sales.

Our future revenues are unpredictable  because the timing and amount of revenues
are subject to a number of factors that make it difficult to estimate  operating
results  prior to the end of a quarter,  which  could  cause our stock  price to
decline.

         We do not  expect to  maintain a  significant  level of  backlog.  As a
result,  product revenues in any quarter are dependent on contracts entered into
or orders booked and shipped in that quarter.  We have  generally  experienced a
trend toward higher order receipt,  and therefore a higher percentage of revenue
shipments,  toward  the end of the last month of a  quarter.  This  trend  makes
predicting  revenues  more  difficult.  The  timing  of  closing  larger  orders
increases the risk of quarter-to-quarter  fluctuation. As we have continued with
our efforts to license our WorldSecure  software to larger enterprises,  in some
cases the size of our orders and the  length of our sales  cycle have  increased
and may increase  further.  If orders  projected  for a specific  customer for a
particular quarter are not realized or revenues are not otherwise  recognized in
that quarter, our operating results for that quarter could be seriously harmed.

Our stock price has been volatile and is likely to remain volatile.

         During  the six  months  ended June 30,  1999,  our stock  price on the
Nasdaq National Market ranged from a high of $5.625 per share to a low of $2.625
per share.  At the close of market on June 30, 1999,  our stock price was

                                      -4-

<PAGE>


$2.875 per share.  Announcements,  litigation developments,  our ability to meet
the expectations of brokerage firms, industry analysts or investors with respect
to our operating and financial  results and general  fluctuations  in the market
may contribute to this volatility.  We may not discover,  or be able to confirm,
revenue or earnings shortfalls until the end of a quarter, which could result in
an  immediate  drop in our  stock  price.  In the  past,  following  periods  of
volatility  in the market  price of a  company's  securities,  securities  class
action litigation has often been instituted against companies with public traded
securities.  Any litigation that is instituted could result in substantial costs
and a diversion of management's attention and resources.

We have a history of losses and we expect to incur additional operating losses.

         We have a history of losses and we expect to incur additional operating
losses in the future.  Our failure to significantly  increase our revenues would
seriously  harm our  business.  We have  experienced  operating  losses  in each
quarterly and annual period since inception and we expect to incur losses in the
future.  As of June 30, 1999, we had an accumulated  deficit of $31,323,000.  We
expect to significantly  increase our sales and marketing,  product  development
and general and administrative expenses. With these additional expenses, we must
significantly increase our revenues in order to become profitable.  As a result,
we expect to incur losses for the  foreseeable  future.  Our expense  levels are
relatively  fixed and are based, in part, on expectations as to future revenues.
We expect our revenues to vary. If revenue  levels fall below our  expectations,
our net loss will increase  because only a small portion of our expenses  varies
with our revenues. We may never achieve  profitability,  and if we do, we cannot
ensure that we will sustain or increase it.

Our business strategy relies heavily upon our WorldSecure products.

         We have  recently  completed a  significant  transition  from our prior
business of licensing  UNIX-based  NetJunction e-mail  productivity  products to
licensing our WorldSecure products,  which operate principally on the Windows NT
platform. As a result, we experienced a shift in product mix from almost 100% of
software license revenue coming from NetJunction products in 1996 to over 90% of
software license revenue coming from Windows NT-based Internet content security,
policy management and e-mail directory products in the first six months of 1999.
We sold our NetJunction  business in July 1999 and now intend to concentrate our
future sales efforts on our e-mail and Internet security  products.  The success
of our strategy of focusing our efforts on providing policy management  software
and services to enterprise  customers,  targeting almost exclusively the Windows
NT-Intel platform, will depend, in part, on the following factors:

         -   our potential  customers' need for, and willingness to purchase and
             implement,   Internet  content   security  and  policy   management
             software;

         -   market acceptance of our WorldSecure products;

         -   our  ability to offer a  cost-effective  product  to our  customers
             under terms acceptable to them;

         -   our  ability  to scale our  products  for the  volume of e-mail and
             Internet use within larger enterprises; and

         -   acceptance  of the  Windows NT  platform  by users and  application
             developers.

If our customers or potential  customers do not budget funds for the purchase of
our e-mail and Internet  security  products,  or if our products do not meet our
customers' needs, our business and operating results will suffer.

We expect that our market will be subject to rapid technological  change and new
product  introductions and enhancements  that we may not be able to address.  We
need to develop and introduce new products, technologies and services.

         The markets for Internet content security, policy management and e-mail
directory   products  are  highly   fragmented  and   characterized  by  ongoing
technological  developments,  evolving  industry  standards and rapid changes in
customer requirements. Our success will depend on our ability to:

         -   offer a broad range of policy management products;

         -   continue to enhance existing products and expand product offerings;

         -   develop  and  introduce  in  a  timely  manner  new  products  with
             technological advances;

         -   respond promptly to new customer requirements;

         -   comply  with  evolving   industry   standards   without  delays  in
             compliance;

                                      -5-

<PAGE>


         -   provide  upgrades and updates to users frequently and at reasonable
             cost; and

         -   remain compatible with Windows NT.

         We may not be able to  successfully  develop  and  market,  on a timely
basis,  enhancements  to our  existing  products or new  products.  In the third
quarter of 1999, we introduced our new  WorldSecure/Web  product for enforcement
and monitoring of Web usage policies.  This new product or other new products or
enhancements  may not adequately  address the changing needs of the marketplace.
New products with new  technological  capabilities  could replace or shorten the
life cycle of our products or cause our  customers to defer or cancel  purchases
of our products.

         Our  long-term  success  depends on our  ability to upgrade  and update
existing product  offerings,  modify and enhance acquired products and introduce
new products that meet our  customers'  needs.  Future  upgrades and updates may
include  additional  functionality,  may respond to user problems or may address
compatibility  problems with changing  operating  systems and  environments.  We
believe that our ability to provide these upgrades and updates frequently and at
low costs is key to our success.  Failure to release  upgrades and updates could
harm our business,  results of operations and financial condition. We may not be
successful in these efforts. In addition,  future changes in Windows NT or other
popular operating systems could cause compatibility  problems with our products.
Further,  delays in the introduction of future versions of operating  systems or
lack of market  acceptance of these future versions would delay or reduce demand
for our  future  products  that were  designed  to  operate  with  these  future
operating systems. Our failure to introduce in a timely manner new products that
are compatible  with  operating  systems and  environments  preferred by desktop
computer users would harm our business and operating results.

Product development delays and errors in our software could harm our business.

         We may continue to experience delays in software development as we have
at times in the past. Complex software products like ours may contain undetected
errors or version  compatibility  problems,  particularly  when first  released,
which  could  delay  or  cost  us our  market  acceptance.  In the  past we have
discovered  errors in our software and some of our future  releases and products
may also contain  errors.  Difficulties  and delays  associated with new product
introductions,  performance or  enhancements  could seriously harm our business,
financial condition and results of operation.

If we do  not  comply  with  emerging  industry  standards,  or if no  standards
develop, our business could suffer.

         Our  product  development  efforts  are  impacted  by the  adoption  or
evolution of industry  standards.  For example, no uniform industry standard has
developed in the market for encryption security products.  As industry standards
are adopted or evolve,  we may have to modify  existing  products or develop and
support new versions of existing products.  In addition, if no industry standard
develops,  our products and our  competitors'  products  could be  incompatible,
which could prevent or delay overall  development of the market for a particular
product.  If our  products  fail to comply with  existing  or evolving  industry
standards in a timely fashion, our business,  results of operation and financial
condition could be harmed.

We sell our products through  intermediaries,  who may not vigorously market our
products or may have difficulty in timely paying for purchased products.  If our
relationships with these intermediaries are not successful,  we may not generate
sufficient revenues to sustain or grow our business.

         We market a  significant  portion of our products to end-users  through
intermediaries, including distributors, resellers and value-added resellers.

         Our distributors may sell other products that are  complementary to, or
compete with, our products.  While we encourage our distributors to focus on our
products  through  market and  support  programs,  these  distributors  may give
greater  priority to  products of other  suppliers,  including  competitors.  We
generally record sales to distributors when the product is shipped.

         Some of our distributors have experienced or are experiencing  economic
difficulties, which may interfere with our collection of accounts receivable. We
regularly review the collectibility and credit worthiness of our distributors to
determine  an  appropriate   allowance  for  doubtful  accounts   reserve.   Our
uncollectible accounts could exceed our current or future allowance for doubtful
accounts reserve, which would harm our operating results.

         In the fourth quarter of 1998, we terminated our relationship  with the
distributor of our products in Japan.  We have not yet engaged a new distributor
of our products in Japan. Identifying, engaging and training distributors of our
products  is  a  long  and  difficult  process  and  requires  a  commitment  of
significant time by our management

                                      -6-

<PAGE>


and employees.  If we are unable to engage and retain distributors and resellers
of our  products  in the  future,  we may  not be able to  sustain  or grow  our
business.

We depend on revenue from our WorldSecure products.  Variations in the volume of
sales will cause  fluctuations in our operating  results,  which could cause our
stock price to decline.

         We  currently  derive a majority of our revenues  from our  WorldSecure
product  line.  These  products  are  expected  to  continue  to  account  for a
significant  portion of our net revenue for the foreseeable  future.  Because of
this concentration of revenue, a decline in demand for or in the prices of these
products  as a result  of  competition,  technological  change,  a change in our
pricing model,  inclusion of Internet content  security,  policy  management and
e-mail  directory  features as a standard  part of hardware or operating  system
software or other  software,  or a maturation in the markets for these products,
could harm our business.

         We may in the future  change the prices we charge for our  products  or
the manner and timing of license fees for our  products.  Changes in our product
pricing model could lead to  significant  decreases in our revenues in the short
term and could  cause our stock  price to decline.  Customer  resistance  to any
future  change  in our  prices or our  pricing  structures  could  also harm our
business and operating results.

If the markets for  Internet  content  security,  policy  management  and e-mail
directory products do not evolve as we anticipate, our business could suffer.

         The markets for our Internet content  security,  policy  management and
e-mail  directory  products are evolving,  and their growth depends upon broader
market acceptance of this software.  Although the number of personal  computers,
or PCs, attached to large-area networks has increased dramatically, the Internet
security and policy management  markets continue to be emerging  markets.  These
markets may not continue to develop or may not develop rapidly enough to benefit
our business  significantly.  If our  customers  or  potential  customers do not
budget sufficient resources to purchase and implement our products, our business
will suffer.

         In  addition,  there are a number of potential  approaches  to Internet
security and policy  management,  including  the  incorporation  of security and
management tools into network  operating  systems.  Therefore,  even if Internet
security  and  policy  management  tools gain  broader  market  acceptance,  our
products  may not be selected by  potential  purchasers.  To the extent that the
electronic mail and Internet security markets do continue to develop,  we expect
that competition will increase.

We are subject to intense  competition  in the  Internet  content  security  and
policy  management  markets and we expect to face  increased  competition in the
future.

         The markets for our products are intensely  competitive,  and we expect
competition  to  increase  in the  near-term.  We  believe  that  the  principal
competitive factors affecting the markets for our products include:

         -   performance;

         -   functionality;

         -   scalability;

         -   customer support;

         -   breadth of product line;

         -   frequency of upgrades and updates;

         -   integration of products;

         -   manageability of products;

         -   brand name recognition; and

         -   price.

         Some of our competitors have longer operating  histories,  greater name
recognition,  larger technical staffs,  established  relationships with hardware
vendors and greater financial,  technical and marketing resources. These factors
may provide our  competitors  with an  advantage  in  penetrating  the  original
equipment manufacturer, or OEM, market with our competitors' electronic mail and
Internet  security  products.  As is the case in many  segments of the  software
industry,  we have  been  encountering,  and we  expect  to  further  encounter,
increasing competition.  This increased competition could reduce average selling
prices and could decrease our profit margins. Competitive pressures could result
not only in price reductions but also in a decline in sales volume,  which could
cause our

                                      -7-

<PAGE>


business to suffer. In addition, competitive pressures may make it difficult for
us to maintain or exceed our historic growth rate.

         The markets for electronic  mail and Internet  security are fragmented,
and several  companies offer products that attempt to address all or some of the
needs  addressed by our products.  Our  principal  competitors  include  Content
Technologies  and  Trend  Micro,  as  well as  numerous  smaller  companies  and
shareware authors that may in the future develop into stronger competitors or be
acquired by larger companies or become consolidated into larger competitors.

         As the electronic mail and Internet  security markets  develop,  we may
face increased  competition  from these  companies,  as well as other  companies
seeking to enter the market. There may be additional consolidation of the e-mail
and Internet  security markets around a smaller number of companies who are able
to provide the necessary software and support capabilities.  In addition, to the
extent that we are successful in developing our  WorldSecure  products  designed
around a  centralized  management  for the Windows NT  platform,  we will likely
compete  with large  computer  systems  management  companies  such as  Computer
Associates,  IBM  and  Microsoft.  We may  be  unable  to  continue  to  compete
effectively  against  existing  and  potential  competitors,  many of whom  have
substantially greater financial,  technical, marketing and support resources and
name recognition than we do. In addition,  software  companies who currently use
traditional  distribution  methods  may in the  future  decide to  compete  more
directly with us by utilizing electronic software distribution.

We have recently experienced significant turnover in senior management.  We must
retain and attract key personnel.

         In August 1999,  Bernard  Harguindeguy  resigned as President and Chief
Executive  Officer of Worldtalk,  and we are currently engaged in a search for a
new Chief  Executive  Officer.  Our ability to achieve our revenue and operating
performance  objectives  will depend in large part on our ability to attract and
retain a new Chief Executive Officer and other technically  qualified and highly
skilled  engineering,  sales,  consulting,  marketing and management  personnel.
Competition  for people to fill these  management and other positions is intense
and is expected to remain so for the foreseeable  future.  We may not be able to
attract or retain a new Chief Executive  Officer with the appropriate  skills to
achieve  our  corporate  objectives.  Our failure to hire and retain a new Chief
Executive  Officer and other key employees could seriously harm our business and
operating results. In 1998 and 1999, we hired new executive officers to fill the
positions of Chief  Financial  Officer,  Vice  President,  Engineering  and Vice
President,  Sales.  Significant  turnover  of  employees,  particularly  in  key
positions,  can be disruptive  and can result in departures of other  employees,
which could harm our business.

         We rely,  and will  continue to rely,  on a number of key technical and
management  employees.  While employees are required to sign standard agreements
concerning  confidentiality  and  ownership of  inventions,  our  employees  are
generally not otherwise  subject to employment  agreements or to  noncompetition
covenants.  If any  of  our  key  employees  leave,  our  business,  results  of
operations and financial condition could suffer. Furthermore, we do not maintain
life insurance policies on our key employees.

Competitors may include  products  similar to ours in their hardware or software
and render our products obsolete.

         Vendors of hardware and of operating  system software or other software
(such as  firewall or e-mail  software)  may  enhance  their  products or bundle
separate products to include policy management software similar to our products.
The widespread  inclusion of products that perform the same or similar  function
as our products  within  computer  hardware or other  software  could render our
products  obsolete and  unmarketable.  Furthermore,  even if these  incorporated
products are inferior or more limited than our products,  customers may elect to
accept the  incorporated  products rather than purchase our products.  If we are
unable to develop new  products to further  enhance  operating  systems or other
software and to successfully  replace any obsolete products,  our business could
suffer.

Our customers may cancel or delay their  purchases of our products,  which could
harm our business. Our lengthy sales cycle could harm our quarterly results.

         Our  products  may be  considered  to be capital  purchases  by certain
customers or prospective  customers.  Capital purchases are often  discretionary
and, therefore,  are canceled or delayed if the customer  experiences a downturn
in its business or prospects or as a result of economic  conditions  in general.
Any cancellation or delay could harm our results of operations.

         In addition,  the length of our sales cycle varies with the size of the
account.  As we continue to focus a significant part of our sales efforts on the
sale of our  WorldSecure  products  to larger  companies,  our  sales  cycle has

                                      -8-

<PAGE>


lengthened  and may  continue  to  lengthen.  Sales  of large  complex  products
frequently require a long education process and significant technical evaluation
and  commitment  of capital and other  resources.  Moreover,  these sales may be
subject to the risk of delays  associated  with  customers'  internal budget and
other  procedures  for  approving  large  capital  expenditures,  deploying  new
technologies  within their network and testing and  accepting  new  technologies
that  affect  key  operations.  Because  of these  longer  sales  cycles and the
potential large size of such orders to these larger enterprises,  if anticipated
orders are not realized or revenues are not otherwise recognized in a particular
quarter, our operating results for that quarter could suffer.

If we are unable to attract,  train and retain an  effective  sales  force,  our
business will suffer.

         We need to expand  our sales  operations  in order to  increase  market
acceptance and  penetration of our  WorldSecure  product line.  Competition  for
qualified  sales  personnel  is  intense  and we may not be able to hire  enough
qualified  sales  personnel in the future.  Our products and services  require a
sophisticated  sales effort  targeted at senior  management  of our  prospective
customers.  New hires in our sales team require extensive training and typically
take at least six months to achieve  full  productivity.  In  addition,  we have
limited experience marketing our products broadly to a large number of potential
partners.  If we cannot  attract,  train and retain a strong  sales  force,  our
business and operating results will be harmed.

Changing  regulatory  and other  requirements  in the  healthcare  and financial
industries could harm our business.

         Our success at  licensing  our products to large  organizations  in the
healthcare and financial  industries depends, in part, on our ability to respond
to regulations and standards  governing these industries.  If new regulations or
standards  are imposed that affect the use of electronic  communications  or the
Internet within these  industries,  we may be required to modify our products to
incorporate these new regulations and standards.  If we are unable to respond to
these  changes,  or if our  response is too slow or is  inadequate,  we may lose
customers in these industries and our business would be harmed.

We rely on the continued  prominence of Microsoft  technology and the Windows NT
platform.

         Although  we may support  other  operating  systems in the future,  the
majority of our revenues  comes from sales of our products for Windows  NT-Intel
based  networks.  Sales of our products would be seriously  harmed by any market
developments that decrease the use of Windows operating environments,  including
the  failure  of users  and  application  developers  to accept  Windows  NT. In
addition,   our  ability  to  develop  products  using  the  Windows   operating
environments  is dependent  on our ability to receive  access to, and to develop
expertise in, current and future  developments by Microsoft.  We may not be able
to gain the necessary access from Microsoft in the future.

We must effectively manage future growth and expansion.

         Any  future  growth  of  our  business   would  continue  to  place,  a
significant strain on our limited personnel, management and other resources. Our
ability to manage any future growth, particularly with the anticipated expansion
of our international business and growth in distribution business,  will require
us to:

         -   attract, train, motivate and manage new employees successfully;

         -   effectively integrate new employees into our operations; and

         -   continue  to improve our  operational,  financial,  management  and
             information systems and controls.

         If we grow, our management systems currently in place may be inadequate
or we may not be able to effectively manage this growth.

We face risks associated with acquisition transactions.

         The software  industry has experienced,  and is expected to continue to
experience,  a  significant  amount  of  consolidation.  As part  of our  growth
strategy, we may buy or make investments in, complementary  companies,  products
and technologies.

         The integration of transactions  involves a complex, time consuming and
expensive  process.  Acquisitions  involve a number of risks such as  geographic
distance  between  the  companies,   the  complexity  of  the  technologies  and
operations being integrated,  the consolidation of duplicative  facilities,  the
ability to attract and retain key management and other personnel and the ability
to combine disparate corporate cultures. If we cannot successfully integrate any
acquisition,  we may lose all or a portion of our  investment,  which could harm
our business.

                                      -9-

<PAGE>


         In  1997,  1998 and  1999,  we  incurred  charges  associated  with our
acquisition of Deming Software Inc. We will continue to incur a portion of these
charges through the year 2000. Our available cash and our securities may be used
to buy or invest in  companies or  products,  which could result in  significant
acquisition-related  charges  to  earnings  and  dilution  to our  stockholders.
Moreover,  if we buy a company,  we may have to incur or assume  that  company's
liabilities,  including liabilities that are unknown at the time of acquisition,
which may result in serious harm to our business.

We rely  heavily on our  intellectual  property  rights which offer only limited
protection against potential infringers.

         Our  success  depends   significantly  upon  our  proprietary  software
technology.  We rely on a combination of contractual rights,  trademarks,  trade
secrets,  patents and copyrights to establish and protect  proprietary rights in
our software.  However,  these  protections may be inadequate or competitors may
independently develop technologies or products that are substantially equivalent
or  superior  to  our  products.  We do  not  typically  obtain  signed  license
agreements  from our  corporate,  government  and  institutional  customers  who
license products directly from us. Rather, we include an electronic version of a
shrink-wrap  license in all of our  electronically  distributed  software  and a
printed  license in the box for our  products  distributed  through  traditional
distributors  in order to  protect  our  copyrights  and trade  secrets in those
products.  Since none of these  licenses are signed by the licensee,  many legal
authorities  believe that such licenses may not be enforceable under the laws of
many states and foreign  jurisdictions.  In  addition,  the laws of some foreign
countries  either  do not  protect  these  rights at all or offer  only  limited
protection  for these rights.  The steps taken by us to protect our  proprietary
software  technology  may be  inadequate  to  deter  misuse  or  theft  of  this
technology.  Changing legal interpretations of liability for unauthorized use of
the  our  software,   or  lessened  sensitivity  by  corporate,   government  or
institutional  users to avoiding  infringement of intellectual  property,  could
harm our business, results of operations and financial condition.

We may be found to  infringe  proprietary  rights of others and  therefore  face
litigation related to our proprietary technology and rights.

         There has been substantial  litigation regarding  intellectual property
rights of technology  companies.  Any  litigation to which we may become a party
could harm our business,  results of operation and financial condition.  Adverse
determinations in any litigation could:

         -   result in the loss of our proprietary rights;

         -   subject us to significant liabilities;

         -   require us to seek licenses from third parties; or

         -   prevent us from producing or selling our products.

         The litigation process is subject to inherent  uncertainties and we may
not  prevail  in these  matters,  or we may be unable to  obtain  licenses  with
respect to any patents or other  intellectual  property  rights that may be held
valid or infringed  upon by us or our  products.  Uncertainties  inherent in the
litigation   process  involve,   among  other  things,  the  complexity  of  the
technologies  involved,  potentially adverse changes in the law and discovery of
facts unfavorable to us.

         In  addition,  as we may acquire a portion of software  included in our
products from third parties,  our exposure to infringement  actions may increase
because we must rely upon such third  parties as to the origin and  ownership of
any software being acquired.  Similarly,  exposure to  infringement  claims will
increase  to the extent  that we employ or hire  additional  software  engineers
previously  employed by  competitors,  notwithstanding  measures  taken by these
competitors to protect their intellectual  property.  In the future,  litigation
may be necessary  to enforce and protect  trade  secrets and other  intellectual
property  rights  that we own.  We may also be subject to  litigation  to defend
against claimed  infringement of the rights of others or determine the scope and
validity of the proprietary  rights of others.  This litigation  could be costly
and cause  diversion of management's  attention,  either of which could harm our
business, results of operations and financial condition.

Our international  operations  subject us to a number of risks inherent in doing
business in foreign countries.

         Net revenue from international  licenses represented  approximately 18%
of our net  revenue in the first six months of 1999,  39% of our net  revenue in
1998 and 19% of our net  revenue  in 1997.  Historically,  we have  relied  upon
independent agents and distributors to market our products  internationally.  We
expect that  international  revenues  will continue to account for a significant
percentage  of net  revenue.  Although  sales  of  our  products  are

                                      -10-

<PAGE>


typically  denominated  in U.S.  dollars,  there  are a number  of  other  risks
inherent in international operations. These risks include:

         -   lengthy payment cycles;

         -   greater difficulty in accounts receivable collection;

         -   unexpected changes in regulatory requirements;

         -   seasonality  due to the  slowdown in European  business  activities
             during the third quarter;

         -   tariffs and other trade barriers;

         -   export restrictions on our encryption and other security products;

         -   uncertainties   relative   to  regional   economic   circumstances,
             including the current economic turbulence in Asia;

         -   political  instability  in  emerging  markets and  difficulties  in
             staffing; and

         -   managing foreign operations.

         These  factors  may  harm our  future  international  license  revenue.
Further,  in  countries  with  a  high  incidence  of  software  piracy,  we may
experience a higher rate of piracy of our products.

         In  addition,  a portion of our  international  revenue is  expected to
continue to be generated through independent agents.  Since these agents are not
our employees and are not required to offer our products  exclusively,  they may
discontinue  marketing our products entirely.  Also, we may have limited control
over these  agents,  limited  access to the names of the customers to whom these
agents sell its products and limited  knowledge of the information  provided by,
or  representations  made by, these agents to its  customers.  We terminated our
relationship  with our Japanese  distributor  in 1998 and have not yet engaged a
new distributor in Japan.

Actual or perceived security breaches could harm our business.

         The secure  transmission  and management of proprietary or confidential
information  over the Internet  and via e-mail is  essential  to  establish  and
maintain  confidence  in  the  WorldSecure  product  line.  Therefore,  security
concerns and  security  breaches of our and our  customers'  network or computer
security may impair the perceived reliability of our products and could harm our
business and operating  results.  We cannot guarantee that our security measures
will prevent security breaches.  In the event that a party is able to circumvent
our  security  systems  and  cause  interruptions  in ours  and  our  customers'
operations by creating  viruses to sabotage or otherwise  attack our products or
steal digital content,  customers'  computer systems could be damaged and demand
for our  software  products  may  suffer.  In  addition,  we may be  subject  to
litigation claiming damages related to an actual or perceived security breach in
the future. Our insurance  policies carry low coverage limits,  which may not be
adequate to reimburse us for losses  caused by security  breaches.  Any security
breach could harm our business and operating results.

The  cryptography  technology  in our products is subject to security  risks and
export restrictions and may become obsolete.

         Certain of our network  security  products,  technology  and associated
assistance are subject to export restrictions  imposed by the U.S. Department of
State and the U.S. Department of Commerce.  These restrictions permit the export
of encryption products so long as certain requirements are met, but prohibit the
export of these  products to countries  deemed  hostile by the U.S.  Government.
U.S. export  regulations  regarding the export of encryption  technology require
either a transactional  export license or the granting of Department of Commerce
Commodity jurisdiction. As result of this regulatory regime, foreign competitors
facing less stringent  controls may be able to compete more  effectively than we
can in the global market. While we have obtained approval from the Department of
Commerce to export to certain  end users,  the U.S.  Government  may not approve
pending or future export  license  requests.  Further,  the list of products and
countries for which export  approval is required,  and the  regulatory  policies
with respect  thereto,  may be revised from time to time.  Failure to obtain the
required  licenses or the costs of compliance  could diminish our  international
revenues.

         In addition, some of our network security products are dependent on the
use of public key cryptography technology.  This technology depends in part upon
the application of certain  mathematical  principles.  The security  afforded by
public key cryptography  technology is based on our belief that circumvention or
compromise of this  technology is difficult.  Should an easy method be developed
for  circumventing  or  compromising  the  encryption  techniques,  the security
afforded by encryption  products using public key cryptography  technology would
be

                                      -11-

<PAGE>


reduced or eliminated.  Furthermore,  any significant  advance in techniques for
attacking  cryptographic  systems  could also render some or all of our existing
products and services obsolete or unmarketable.

Product  liability  claims  asserted  against  us in the  future  could harm our
business.

         Our software  products are used to protect and manage computer  systems
and networks that may be critical to  organizations.  As a result,  our sale and
support of these products  involves the risk of potential  product liability and
related  claims.  Our license  agreements with our customers  typically  contain
provisions designed to limit our exposure to potential product liability claims.
It is possible,  however,  that the limitation of liability provisions contained
in these  license  agreements  may not be  effective  under the laws of  certain
jurisdictions,  particularly in circumstances  involving  unsigned  licenses.  A
product  liability claim brought against us could harm our business,  results of
operations and financial condition.

We face risks associated with U.S. government contracting.

         We expect that in the near term, a portion of our revenues  will result
from  contracts  with  agencies  of the U.S.  government.  We  believe  that the
willingness of these government  agencies to enter into future contracts with us
will in part be dependent upon our continued ability to meet their standards and
expectations.  However,  we may  be  unable  to  procure  additional  government
contracts.  In addition,  our products must be certified by the U.S.  government
prior to their adoption or use by certain government agencies or departments. If
we fail to  receive  government  certification  of our  products,  we will  have
limited  opportunities  to sell to  government  agencies  and our  business  and
operating results may be harmed.

Year 2000 issues could harm our business.

         Many currently  installed  computer  systems and software  products are
coded to  accept,  store,  or report  only two digit  year  entries in date code
fields.  Beginning in the year 2000,  these date code fields will need to accept
four digit entries to  distinguish  21st century dates from 20th century  dates.
The year 2000  problem  arises in  programs  that were  written  with two digits
instead of four. As a result,  computer  systems and software used by companies,
including us and our vendors and customers, will need to operate properly in the
year 2000 and beyond.  Although we have tested our  software and believe that it
is year 2000  compliant,  we may in the future detect  problems  relating to the
year 2000, which could seriously harm our business.

         In addition, we and the third parties with whom we conduct business may
utilize  equipment or software that may not be year 2000  compliant.  Failure of
our or any of this  equipment  or software to operate  properly in the year 2000
and beyond  could  result in,  among  other  things,  unanticipated  expenses or
efforts  to remedy any  problems,  which  could  harm our or such third  party's
respective business. Furthermore, companies may spend more money to evaluate and
correct  their  own  equipment  or  software  for year  2000  compliance.  These
increased  expenditures may result in fewer funds available to purchase products
and services such as those offered by us, which could harm our business.

We rely on a limited number of third-party  suppliers,  who may not consistently
meet our business needs.

         We  rely  on  third-party   suppliers  to  provide  certain  technology
components that we incorporate into our products. In particular,  the encryption
and anti-virus  technology in our products come from third  parties.  If we were
unable to obtain licenses to the  technologies or to future versions or upgrades
of these  technologies,  we would have to identify and license new  technologies
and would potentially have to redesign portions of our products around these new
technologies.  Substitute  technologies  may not be available upon  commercially
reasonable  terms,  and our failure to obtain licenses to necessary  third-party
software could seriously harm our business.

Provisions of Delaware law may inhibit  potential  acquisition  bids which could
decrease  the  market  price for our  common  stock and  prevent  changes in our
management.

         Our  board of  directors  has the  authority  to issue up to  6,500,000
shares of  preferred  stock and to  determine  the price,  rights,  preferences,
privileges and  restrictions,  including voting rights,  of those shares without
any further vote of action by its stockholders. The issuance of preferred stock,
while providing desirable  flexibility in connection with possible  acquisitions
and other corporate purposes,  could have the effect of making it more difficult
for a third party to acquire a majority of the outstanding voting stock.

         Certain provisions of Delaware law and our certificate of incorporation
and bylaws,  such as a classified  board,  could delay or make a merger,  tender
offer  or  proxy  contest  involving  Worldtalk  more  difficult.   While  these
provisions are intended to enable our board of directors to maximize stockholder
value,  they may have the effect of

                                      -12-

<PAGE>


discouraging  takeovers  which  may  not  be in the  best  interest  of  certain
stockholders.  These provisions could cause a decline in the market value of our
common stock.

We are significantly influenced by our existing stockholders.

         Stockholders  who own in excess of 5% of our  stock  together  with our
executive officers and directors and their affiliates,  beneficially own, in the
aggregate, approximately 55% of our outstanding common stock. As a result, these
stockholders will be able to control or exercise significant  influence over all
matters requiring stockholder approval,  including the election of directors and
approval of significant corporate  transactions,  which could have the effect of
delaying or preventing a third party from acquiring control over us.

Our prospects for obtaining additional financing, if required, are uncertain and
failure to obtain  needed  financing  could affect our ability to pursue  future
growth.

         We  believe  that our  cash  balances  and  credit  facilities  will be
sufficient to meet our anticipated working capital and capital expenditure needs
for at least the next 12 months.  After  that,  we may need to raise  additional
funds,  and  additional  financing  may  not be  available  on  terms  that  are
acceptable  to us,  if at all.  This  could  seriously  harm  our  business  and
operating  results.  Furthermore,  if we  raise  additional  funds  through  the
issuance of equity or convertible debt securities,  the percentage  ownership of
our  stockholders  would be reduced  and these  securities  might  have  rights,
preferences  and  privileges  senior to those of our  current  stockholders.  If
adequate  funds are not  available on  acceptable  terms,  we may not be able to
develop or enhance our products or services, fund our expansion,  take advantage
of future  opportunities,  or respond to competitive  pressures or unanticipated
requirements.

If we do not remain  listed on the Nasdaq  Stock  Market,  our stock price could
decline.

         In the first half of 1999,  Worldtalk was temporarily out of compliance
with the  criteria  for  continued  listing  of our  common  stock on the Nasdaq
National  Market.  Following  the closing of a private  placement  of our common
stock in July 1999 and a hearing before Nasdaq,  we received  confirmation  from
Nasdaq that we have  returned to  compliance  with the National  Market  listing
criteria. Although we are currently in compliance with these criteria, we may in
the future fall out of  compliance  and have our common stock  delisted from the
National  Market.  Any future delisting action could harm our business and cause
our stock price to decline.


                           FORWARD-LOOKING STATEMENTS

         This prospectus contains forward-looking  statements within the meaning
of  Section  27A of the  Securities  Act and  Section  21E of the  Exchange  Act
relating to future events or financial results. These forward-looking statements
include statements  indicating that we believe,  we expect or we anticipate that
events may occur or trends may  continue,  and  similar  statements  relating to
future events or financial results. These forward-looking statements are subject
to  material  risks and  uncertainties  as  indicated  under the  caption  "Risk
Factors."  Actual  results  could  vary  materially  as a result  of a number of
factors  including  those  disclosed  in "Risk  Factors"  and  elsewhere in this
prospectus.


                                 USE OF PROCEEDS

         We will not receive any of the proceeds  from the sale of shares by the
selling stockholders.

                                      -13-

<PAGE>


                              SELLING STOCKHOLDERS

         The following table sets forth certain information we know with respect
to the beneficial  ownership by the selling  stockholders our common stock as of
August 10, 1999.  Except as discussed below, the selling  stockholders  have not
had any position,  office or other material relationship with us within the past
three years.

         Applicable  percentage  ownership  in the  following  table is based on
14,286,772  shares of common stock  outstanding as of August 10, 1999 and treats
as  outstanding  all  warrants  held by the  particular  stockholder  since each
warrant is  currently  exercisable.  The table also treats as  outstanding,  for
purposes of  calculating  each specific  stockholder's  percent  ownership,  all
options held by the stockholder that are exercisable within 60 days after August
10, 1999.

         The table assumes that the selling  stockholders sell all of the shares
offered by them in this offering.  However, we are unable to determine the exact
number of shares that will actually be sold or when or if such sales will occur.
We will not receive the proceeds of any shares sold under this  prospectus.  The
selling  stockholders have advised us that they are the beneficial owners of the
shares being offered.

<TABLE>
         Unless otherwise indicated,  the address of each selling stockholder is
c/o Hilal Capital Management LLC, 60 East 42nd Street,  Suite 1946, New York, NY
10165.

<CAPTION>
                                                   Shares Beneficially                        Shares Beneficially
                                                  Owned Before Offering                       Owned After Offering
                                                  --------------------                        --------------------
                                                                           Shares Being
Name                                              Number       Percent       Offered            Number    Percent
- ----                                              ------       -------       -------            ------    -------
<S>                                             <C>              <C>        <C>                <C>           <C>
Hilal Capital Associates LLC (1)                1,792,000        12.0%      1,792,000               0          0

Highbridge International (2)                      986,000         6.7         969,500          16,500        0.1%

Hilal Capital International, Ltd. (3)             920,500         6.3         904,000          16,500        0.1

Hilal Capital QP, L.P. (4)                        683,500         4.7         671,500          12,000        0.1

Hilal Capital, L.P. (5)                           268,000         1.9         263,000           5,000          0

Narragansett I, LP (6)                            197,500         1.4         197,500               0          0
c/o Narragansett Asset Management LLC
375 Park Avenue, Suite 1404
New York, New York 10152

Philip Hilal (7)                                  150,000         1.0         150,000               0          0

Narragansett Offshore, Ltd. (8)                    52,500         0.4          52,500               0          0
c/o Leo Holdings, LLC
375 Park Avenue, Suite 1404
New York, New York 10152

Sigma Partners II, L.P. (9)                       707,056         4.9         670,458          36,598        0.3
2884 Sand Hill Road, Suite 121
Menlo Park, CA 94025

Sigma Associates II, L.P. (9)                      86,875         0.6          50,277          36,598        0.3
2884 Sand Hill Road, Suite 121
Menlo Park, CA 94025

<FN>
- ------------------------------------

                                      -14-

<PAGE>


(1)  This number includes  597,333 shares of common stock issuable upon exercise
     of a  warrant.  Paul  Hilal,  a member  of our board of  directors  and the
     Chairman  of the  Board of  Worldtalk,  is a  non-managing  member of Hilal
     Capital  Partners  LLC,  which is the  general  partner  of  Hilal  Capital
     Associates  LLC,  Hilal Capital QP, L.P. and Hilal  Capital,  L.P. Peter K.
     Hilal,  M.D.,  the brother of Paul Hilal,  is the managing  member of Hilal
     Capital Partners LLC.

(2)  This number Includes  323,167 shares of common stock issuable upon exercise
     of a warrant.  Hilal Capital  Management LLC is the investment  manager for
     Highbridge International,  Ltd. and Hilal Capital International, Ltd. Peter
     K. Hilal, M.D. is the managing member of Hilal Capital Management LLC.

(3)  This number includes  301,333 shares of common stock issuable upon exercise
     of a warrant.

(4)  This number includes  223,833 shares of common stock issuable upon exercise
     of a warrant. Paul Hilal is a non-managing member of Hilal Capital Partners
     LLC, which is the general partner of Hilal Capital QP, L.P.

(5)  This number  includes  87,667 shares  shares of common stock  issuable upon
     exercise of a warrant. Paul Hilal is a non-managing member of Hilal Capital
     Partners LLC, which is the general partner of Hilal Capital, L.P.

(6)  This number  includes  65,833 shares of common stock issuable upon exercise
     of a warrant.

(7)  This number  includes  50,000 shares of common stock issuable upon exercise
     of a warrant. Philip Hilal is the brother of Paul Hilal.

(8)  This number  includes  17,500 shares of common stock issuable upon exercise
     of a warrant.

(9)  These figures  include 24,098 shares held by Wade Woodson and 12,500 shares
     subject to options held by Mr. Woodson that are exercisable  within 60 days
     after August 10, 1999. Mr. Woodson,  a director of Worldtalk,  is a general
     partner of Sigma Management II, L.P., the general partner of Sigma Partners
     II, L.P. and Sigma Associates II, L.P.
</FN>
</TABLE>


         Paul Hilal does not hold voting or dispositive  control over any shares
or  warrants  owned  of  record  by Hilal  Capital  Associates  LLC,  Highbridge
International,  Hilal Capital International, Ltd., Hilal Capital QP, L.P., Hilal
Capital,  L.P. or Philip Hilal. Paul Hilal disclaims beneficial ownership of all
of these shares and warrants.

                              PLAN OF DISTRIBUTION

         Through a private  placement  in July 1999,  the  selling  stockholders
acquired the shares of common stock and the common stock  issuable upon exercise
of  warrants.  Each  selling  stockholder  is  bound  by a  registration  rights
agreement with Worldtalk. To our knowledge, none of the selling stockholders has
entered into any  agreement,  arrangement or  understanding  with any particular
broker or market maker with respect to the shares offered under this prospectus,
nor  do we  know  the  identity  of the  brokers  or  market  makers  that  will
participate in the offering.

         The shares of common stock may be offered and sold from time to time by
the selling  stockholders  or by their pledgees,  donees,  transferees and other
successors in interest. The selling stockholders will act independently of us in
making decisions with respect to the timing,  manner and size of each sale. Such
sales  may be made  over  the  Nasdaq  National  Market  or  otherwise,  at then
prevailing  market prices,  at prices related to prevailing  market prices or at
negotiated prices. The shares may be sold by one or more of the following:

     o   a  block  trade  in  which  the  broker-dealer  engaged  by  a  selling
         stockholder  will  attempt to sell the shares as agent but may position
         and  resell a  portion  of the block as  principal  to  facilitate  the
         transaction;

     o   purchases by the  broker-dealer  as principal and resale by such broker
         or dealer for its account pursuant to this prospectus; and

     o   ordinary  brokerage  transactions  and transactions in which the broker
         solicits purchasers.

         Each selling  stockholder has advised  Worldtalk that it has not, as of
the date hereof,  entered into any arrangement with a broker-dealer for the sale
of shares through a block trade, special offering, or secondary  distribution of
a purchase by a broker-dealer.  In effecting sales,  broker-dealers engaged by a
selling  stockholder  may  arrange  for  other  broker-dealers  to  participate.
Broker-dealers  will receive commissions or discounts from a selling stockholder
in amounts to be negotiated immediately prior to the sale.

         In connection with distributions of the shares or otherwise,  a selling
stockholder  may  enter  into  hedging  transactions  with  broker-dealers.   In
connection with these transactions,  broker-dealers may engage in short sales of
the shares in the course of hedging  the  positions  they  assume  with  selling
stockholder.  A selling stockholder may also sell shares short and redeliver the
shares to close out such short positions.  A selling  stockholder may also enter
into option or other transactions with broker-dealers which require the delivery
to the  broker-dealer  of the  shares,

                                      -15-

<PAGE>


which the broker-dealer may resell or otherwise  transfer under this prospectus.
A selling  stockholder may also loan or pledge the shares 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 under this prospectus.

         Broker-dealers  or  agents  may  receive  compensation  in the  form of
commissions,  discounts or concessions from a selling  stockholder in amounts to
be  negotiated  in  connection  with  the  sale.  Broker-dealers  and any  other
participating  broker-dealers  may be deemed  to be  "underwriters"  within  the
meaning of the Securities Act in connection with the sales,  and any commission,
discount or concession may be deemed to be underwriting discounts or commissions
under the Securities Act. In addition, any securities covered by this prospectus
which  qualify for sale under Rule 144 of the  Securities  Act may be sold under
Rule 144 rather than under this prospectus.

         We have  advised each selling  stockholder  that the  anti-manipulation
rules under the  Exchange  Act may apply to sales of shares in the market and to
the activities of the selling  stockholders and their  affiliates.  Each selling
stockholder  has  advised us that  during  such time as it may be engaged in the
attempt to sell shares registered, it will:

     o   not engage in any stabilization  activity in connection with any of our
         securities;

     o   not bid for or purchase any of our  securities or any rights to acquire
         our securities,  or attempt to induce any person to purchase any of our
         securities or rights to acquire our securities  other than as permitted
         under the Exchange Act;

     o   not  effect any sale or  distribution  of the  shares  until  after the
         prospectus shall have been  appropriately  amended or supplemented,  if
         required, to set forth the terms thereof; and

     o   effect   all  sales  of  shares  in   broker's   transactions   through
         broker-dealers  acting as agents, in transactions  directly with market
         makers or in privately negotiated transactions where no broker or other
         third party (other than the purchaser) is involved.

         Under certain circumstances,  we have the ability to suspend the use of
this  prospectus  if, in the good faith  judgment of our board of directors,  it
would be seriously  detrimental to us and our stockholders for resales of shares
to be made due to:

     o   the  existence  of  a  material   development  or  potential   material
         development  with respect to or involving  Worldtalk  which we would be
         obligated to disclose in the prospectus,  which disclosure would in the
         good faith judgment of our board of directors be premature or otherwise
         inadvisable  at  such  time  and  would   seriously  harm  us  and  our
         stockholders, or

     o   the  occurrence  of any  event  that  makes any  statement  made in the
         prospectus or any document incorporated or deemed to be incorporated by
         reference  untrue in any material  respect or which requires the making
         of any changes in the prospectus so that it will not contain any untrue
         statement of a material fact required to be stated therein or necessary
         to make the  statements  therein  not  misleading  or omit to state any
         material   fact  required  to  be  stated  or  necessary  to  make  the
         statements,  in the light of the  circumstances  under  which they were
         made, not misleading.

         This offering will terminate on the later of:

     o   July 7, 2001; or

     o   the date on which the accountants to the selling  stockholders  confirm
         that a discount  to market  price  would not be applied to the  selling
         stockholders'   holdings  of  common  stock  for  financial   statement
         valuation purposes.

         This offering  will  terminate  earlier if the all shares  offered have
been sold by the selling stockholders.

         We have agreed to pay the expenses of registering  the shares under the
Securities  Act,  including  registration  and filing fees,  printing  expenses,
administrative  expenses  and certain  legal and  accounting  fees.  The

                                      -16-

<PAGE>


selling  stockholders  will bear all  discounts,  commissions  or other  amounts
payable to underwriters,  dealers or agents,  as well as fees and  disbursements
for legal counsel retained by the selling stockholders.

         We and each selling stockholder have agreed to indemnify each other and
certain other related  parties for certain  liabilities  in connection  with the
registration of the shares offered.

         Upon the  occurrence of any of the following  events,  this  prospectus
will be amended to include additional  disclosure before offers and sales of the
securities in question are made:

     o   to the extent the  securities  are sold at a fixed  price or at a price
         other than the prevailing  market price,  such price would be set forth
         in the prospectus;

     o   if the  securities  are sold in block  transactions  and the  purchaser
         acting  in the  capacity  of an  underwriter  wishes  to  resell,  such
         arrangements would be described in the prospectus;

     o   if any  selling  stockholder  sells to a  broker-dealer  acting  in the
         capacity as an underwriter,  such  broker-dealer  will be identified in
         the prospectus; and

     o   if the  compensation  paid to  broker-dealers  is other  than usual and
         customary  discounts,  concessions  or  commissions,  disclosure of the
         terms of the transaction would be included in the prospectus.


                                  LEGAL MATTERS

         The  validity  of  the  shares  of  common  stock  offered  under  this
prospectus  will be passed upon for  Worldtalk by Fenwick & West LLP, Palo Alto,
California.


                                     EXPERTS

         The  consolidated  financial  statements  and schedule of Worldtalk and
subsidiary  as of  December  31,  1998 and 1997 and for each of the years in the
three-year  period ended December 31, 1998, have been  incorporated by reference
herein and in the  registration  statement  in reliance  upon the report of KPMG
LLP, independent auditors,  incorporated by reference, and upon the authority of
said firm as experts in accounting and auditing.


                              CHANGE IN MANAGEMENT

         In August  1999,  Bernard  Harguindeguy  resigned as  President,  Chief
Executive Officer and a director of Worldtalk.  James Heisch,  Worldtalk's Chief
Financial Officer,  has been appointed as President,  and Paul Hilal, a director
of Worldtalk,  has been appointed Chairman of the Board.  Worldtalk is currently
engaged in a search for a new Chief Executive Officer.


                   DOCUMENTS INCORPORATED BY REFERENCE IN THIS
                                   PROSPECTUS

         This  prospectus  incorporates  documents  by  reference  which are not
presented in or delivered with this prospectus.

         All documents filed by us pursuant to Section 13(a), 13(c), 14 or 15(d)
of  the  Securities  Exchange  Act,  after  the  date  of  this  prospectus  are
incorporated by reference into and to be a part of this prospectus from the date
of filing of those documents.

         You should rely only on the  information  contained in this document or
that we have referred you to. We have not authorized  anyone to provide you with
information that is different.

         We filed the  following  documents  with the  Securities  and  Exchange
Commission and are incorporating them by reference into this prospectus.

     o   Worldtalk's  Quarterly  Report on Form 10-Q for the quarter  ended June
         30, 1999 (SEC file number 0-27886 and filing date August 13, 1999)

                                      -17-

<PAGE>


     o   Worldtalk's  Report on Form 8-K filed on July 20, 1999 (SEC file number
         0-27886)

     o   Worldtalk's  Quarterly  Report on Form  10-Q/A-1 for the quarter  ended
         March 31, 1999 (SEC file number 0-27886 and filing date May 28, 1999)

     o   Worldtalk's  Quarterly  Report on Form 10-Q for the quarter ended March
         31, 1999 (SEC file number 0-27886 and filing date May 17, 1999)

     o   Worldtalk's  Annual Report on Form 10-K for the year ended December 31,
         1998 (SEC file number 0-27886 and filing date March 31, 1999)

     o   Worldtalk's Registration Statement on Form 8-A (SEC file number 0-27886
         and filing  date  March 4, 1996,  which  describes  Worldtalk's  common
         stock)

         Any  statement  contained  in a document  incorporated  or deemed to be
incorporated  by  reference  will be deemed to be  modified  or  superseded  for
purposes of this  prospectus  to the extent that a statement  contained  in this
prospectus  or any  other  subsequently  filed  document  that is  deemed  to be
incorporated  in  this  prospectus  by  reference  modifies  or  supersedes  the
statement. Any statement so modified or superseded will not be deemed, except as
so modified or superseded, to constitute a part of this prospectus.


                       WHERE YOU CAN FIND MORE INFORMATION

         The  documents  incorporated  by  reference  into this  prospectus  are
available  from us upon  request.  We will  provide a copy of any and all of the
information that is incorporated by reference in this prospectus,  not including
exhibits to the information unless those exhibits are specifically  incorporated
by reference into this prospectus,  to any person,  without charge, upon written
or oral request.

         Requests for documents  should be directed to Worldtalk  Communications
Corporation,  Attention:  Investor  Relations,  5155 Old Ironsides Drive,  Santa
Clara, California, 95054, telephone number (408) 567-1500.

         We file  reports,  proxy  statements  and  other  information  with the
Securities and Exchange Commission.  Copies of our reports, proxy statements and
other information may be inspected and copied at the public reference facilities
maintained by the SEC:

Judiciary Plaza             Citicorp Center            Seven World Trade Center
Room 1024                   5000 West Madison Street   13th Floor
450 Fifth Street, N.W.      Suite 1400                 New York, New York  10048
Washington, D.C. 20549      Chicago, Illinois  60661


         Copies of these  materials  can also be obtained by mail at  prescribed
rates from the Public  Reference  Section of the SEC,  450 Fifth  Street,  N.W.,
Washington,  D.C.  20549  or by  calling  the  SEC at  1-800-SEC-0330.  The  SEC
maintains  a  web  site  that  contains  reports,  proxy  statements  and  other
information  regarding  each  of  us.  The  address  of  the  SEC  web  site  is
http://www.sec.gov.

         Worldtalk has filed a registration  statement  under the Securities Act
with the  Securities  and Exchange  Commission  with respect to the shares to be
sold by the selling stockholders.  This prospectus has been filed as part of the
registration statement.  This prospectus does not contain all of the information
set  forth  in  the  registration   statement   because  certain  parts  of  the
registration  statement are omitted in accordance with the rules and regulations
of the SEC. The  registration  statement is available for inspection and copying
as set forth above.

         This prospectus does not constitute an offer to sell, or a solicitation
of an offer to  purchase,  the  securities  offered  by this  prospectus  or the
solicitation  of a proxy,  in any  jurisdiction to or from any person to whom or
from whom it is unlawful to make such offer,  solicitation  of an offer or proxy
solicitation in such  jurisdiction.  Neither the delivery of this prospectus nor
any  distribution  of securities  pursuant to this prospectus  shall,  under any
circumstances,  create  any  implication  that  there  has been no change in the
information  set forth or  incorporated  herein by  reference  or in our affairs
since the date of this prospectus.

                                      -18-

<PAGE>


                                     PART II

                     INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 14. Other Expenses of Issuance and Distribution.

         The  aggregate  estimated  expenses  to be  paid by the  Registrant  in
connection with this offering are as follows:

Securities and Exchange Commission registration fee ..............       $ 5,742
Accounting fees and expenses .....................................         5,000
Legal fees and expenses ..........................................        50,000
Miscellaneous ....................................................         5,258
                                                                         -------
     Total .......................................................       $66,000
                                                                         =======


ITEM 15. Indemnification of Directors and Officers.

         As permitted by Section 145 of the Delaware  General  Corporation  Law,
the  Registrant's   Certificate  of  Incorporation  includes  a  provision  that
eliminates  the personal  liability of its  directors to the  Registrant  or its
stockholders  for monetary  damages for breach of fiduciary  duty as a director,
except for liability  (a) for any breach of a director's  duty of loyalty to the
corporation or its stockholders,  (b) for acts or omissions not in good faith or
that involve  intentional  misconduct  or a knowing  violation of law, (c) under
section 174 of the Delaware  General  Corporation Law or (d) for any transaction
from which the director derived an improper  personal benefit.  In addition,  as
permitted by Section 145 of the Delaware General  Corporation Law, the Bylaws of
the  Registrant  provide that:  (a) the  Registrant is required to indemnify its
directors and executive officers to the fullest extent permitted by the Delaware
General  Corporation  Law; (b) the Registrant may, in its discretion,  indemnify
other  officers,  employees  and  agents  as set forth in the  Delaware  General
Corporation  Law; (c) upon receipt of an  undertaking  to repay such advances if
indemnification  is determined to be unavailable,  the Registrant is required to
advance expenses,  as incurred,  to its directors and executive  officers to the
fullest extent permitted by the Delaware  General  Corporation Law in connection
with a proceeding  (except if a determination is reasonably and promptly made by
the Board of Directors by a majority  vote of a quorum  consisting  of directors
who  were not  parties  to the  proceeding  or,  in  certain  circumstances,  by
independent  legal  counsel  in a written  opinion  that the facts  known to the
decision-making  party  demonstrate  clearly and  convincingly  that such person
acted in bad faith or in a manner  that such  person did not believe to be in or
not opposed to the best interests of the corporation);  (d) the rights conferred
in the Bylaws are not exclusive  and the  Registrant is authorized to enter into
indemnification agreements with its directors,  officers,  employees and agents;
(e) the Registrant may not retroactively  amend the Bylaw provisions relating to
indemnity;  and (f) to the fullest  extent  permitted  by the  Delaware  General
Corporation Law, a director or executive officer will be deemed to have acted in
good faith and in a manner he or she reasonably believed to be in or not opposed
to the best  interests  of the  Registrant,  and,  with  respect to any criminal
action or proceeding, to have had no reasonable cause to believe that his or her
conduct was  unlawful,  if his or her action is based on the records or books of
account of the Registrant or on  information  supplied to him or her by officers
of the  Registrant  in the  course  of their  duties  or on the  advice of legal
counsel for the Registrant or on information or records given or reports made to
the  Registrant by  independent  certified  public  accountants or appraisers or
other experts.

         The Registrant has entered into indemnity  agreements  with each of its
directors  and  executive  officers.   The  indemnity  agreements  provide  that
directors and executive  officers will be  indemnified  and held harmless to the
fullest  possible  extent  permitted  by  law  including  against  all  expenses
(including  attorneys' fees),  judgments,  fines and settlement  amounts paid or
reasonably  incurred by them in any action,  suit or  proceeding,  including any
derivative  action by or in the right of the  Registrant,  on  account  of their
services as  directors,  officers,  employees or agents of the  Registrant or as
directors, officers, employees or agents of any other company or enterprise when
they are  serving  in such  capacities  at the  request of the  Registrant.  The
Registrant  will not be  obligated  pursuant to the  agreements  to indemnify or
advance  expenses to an indemnified  party with respect to proceedings or claims
(a) initiated by the  indemnified  party and not by way of defense,  except with
respect to a  proceeding  authorized  by the Board of Directors  and  successful
proceedings  brought to enforce a right to  indemnification  under the indemnity
agreements,  (b) for any amounts paid in settlement  of a proceeding  unless the
Registrant  consents  to such  settlement;  (c) on  account of any suit in which
judgment is rendered against the indemnified  party for an accounting of profits
made from the purchase or sale by the  indemnified  party of  securities  of the
Registrant pursuant to the provisions of

                                      II-1

<PAGE>


ss.16(b) of the Securities Exchange Act of 1934 and related laws; (d) on account
of conduct by an indemnified  party that is finally adjudged to have been in bad
faith or conduct that the indemnified party did not reasonably believe to be in,
or not opposed to, the best interests of the  Registrant;  (e) on account of any
criminal action or proceeding  arising out of conduct that the indemnified party
had  reasonable  cause to believe was unlawful;  or (f) if a final decision by a
court   having   jurisdiction   in  the  matter   shall   determine   that  such
indemnification is not lawful.

         The  indemnity  agreement  requires a director or executive  officer to
reimburse  the  Registrant  for  expenses  advanced  only  to the  extent  it is
ultimately  determined  that the director or executive  officer is not entitled,
under Delaware law, the Bylaws,  his or her indemnity  agreement or otherwise to
be indemnified for such expenses.  The indemnity  agreement  provides that it is
not  exclusive of any right a director or  executive  officer may have under the
Certificate of Incorporation, Bylaws, other agreements, any majority-in-interest
vote of the stockholders or vote of disinterested  directors,  the Delaware law,
or otherwise.

         The  indemnification   provision  in  the  Bylaws,  and  the  indemnity
agreements  entered into between the  Registrant and its directors and executive
officers,   may  be  sufficiently   broad  to  permit   indemnification  of  the
Registrant's  directors and executive officers for liabilities arising under the
Securities Act.

         As authorized by the Registrant's Bylaws, the Registrant, with approval
by the Registrant's  Board of Directors,  has obtained  directors' and officers'
liability  insurance with a per claim and annual aggregate  coverage limit of $5
million.


ITEM 16. Undertakings.

         The undersigned Registrant hereby undertakes:

                  (1) To file,  during any  period in which  offers or sales are
being made pursuant to this Registration  Statement, a post-effective  amendment
to this Registration Statement:

                           (i) to include  any  prospectus  required  by Section
                  10(a)(3) of the Securities Act of 1933 (the "Securities Act");

                           (ii) to reflect in the prospectus any facts or events
                  arising after the effective date of the registration statement
                  (or the most recent  post-effective  amendment thereof) which,
                  individually  or in the  aggregate,  represent  a  fundamental
                  change  in the  information  set  forth  in  the  Registration
                  Statement  (notwithstanding  the  foregoing,  any  increase or
                  decrease in volume or securities  offered (if the total dollar
                  value of  securities  offered  would not exceed that which was
                  registered)  and any deviation from the low or high end of the
                  estimated  maximum offering range may be reflected in the form
                  of  prospectus  filed  with the  Commission  pursuant  to Rule
                  424(b) if, in the  aggregate,  the changes in volume and price
                  represent  no more than a 20% change in the maximum  aggregate
                  offering price set forth in the  "Calculation  of Registration
                  Fee" table in the effective registration statement); and

                           (iii)  to  include  any  material   information  with
                  respect to the plan of distribution  not previously  disclosed
                  in the  Registration  Statement or any material change to such
                  information in the Registration Statement;  provided, however,
                  that  paragraphs  (1)(i)  and  (1)(ii)  do  not  apply  if the
                  information  required  to  be  included  in  a  post-effective
                  amendment by paragraphs  (1)(i) or (1)(ii) is contained in any
                  periodic  report filed with or furnished to the Securities and
                  Exchange  Commission by the Registrant  pursuant to Section 13
                  or Section 15(d) of the  Securities  Exchange Act of 1934 (the
                  "Exchange  Act") that are  incorporated  by  reference  in the
                  Registration Statement.

                  (2) That, for the purpose of determining  any liability  under
the  Securities  Act,  each  post-effective  amendment  shall  be  deemed  a new
registration  statement  relating to the  securities  offered  therein,  and the
offering of such  securities at that time shall be deemed to be the initial bona
fide offering thereof.

                  (3) To remove from  registration by means of a  post-effective
amendment  any of the  securities  being  registered  which remain unsold at the
termination of the offering.

                                      II-2

<PAGE>


                  (4) That, for purposes of determining  any liability under the
Securities  Act,  each  filing of the  Registrant's  annual  report  pursuant to
Section 13(a) or Section 15(d) of the Exchange Act (and, where applicable,  each
filing of an employee  benefit plan's annual report pursuant to Section 15(d) of
the  Exchange  Act)  that is  incorporated  by  reference  in this  Registration
Statement  shall be deemed to be a new  registration  statement  relating to the
securities  offered  herein,  and the offering of such  securities  at that time
shall be deemed to be the initial bona fide offering thereof.

         Insofar as indemnification for liabilities arising under the Securities
Act may be  permitted to  directors,  officers  and  controlling  persons of the
Registrant  pursuant  to the  provisions  described  under  Item  15  above,  or
otherwise, the Registrant has been advised that in the opinion of the Securities
and  Exchange  Commission  such  indemnification  is  against  public  policy as
expressed in the Securities Act and is, therefore,  unenforceable.  In the event
that a claim  for  indemnification  against  such  liabilities  (other  than the
payment by the Registrant of expenses incurred or paid by a director, officer or
controlling  person of the Registrant in the  successful  defense of any action,
suit or proceeding) is asserted by such director,  officer or controlling person
in connection with the securities being registered,  the Registrant will, unless
in the  opinion  of its  counsel  the matter  has been  settled  by  controlling
precedent,  submit to a court of appropriate  jurisdiction  the question whether
such  indemnification  by it is  against  public  policy  as  expressed  in  the
Securities Act and will be governed by the final adjudication of such issue.

                                      II-3

<PAGE>


ITEM 17.  Exhibits.

         (a) The following exhibits are filed herewith:

   Exhibit
   Number                           Exhibit Title
   ------                           -------------
    3.01     Registrant's Certificate of Incorporation. (1)

    3.02     Registrant's Certificate of Designation. (1)

    3.03     Registrant's Certificate of Elimination. (1)

    4.02     Form of Specimen Common Stock Certificate. (1)

    5.01     Opinion of Fenwick & West LLP regarding  legality of the securities
             being registered.

   23.01     Consent of Fenwick & West LLP (included in Exhibit 5.01).

   23.02     Consent of KPMG LLP, Independent Auditors.

   24.01     Power of Attorney (see Page II-6).

   99.01     Securities Purchase Agreement entered into as of July 7, 1999 among
             the  Registrant and the parties listed on the Schedule of Investors
             attached thereto, with form of Escrow Agreement attached. (2)

   99.02     Registration  Rights  Agreement  entered into on July 7, 1999 among
             the Registrant and the Investors. (2)

   99.03     Form of Warrant issued as of July 7, 1999 to the Investors. (2)

- ------------------
(1)  Previously  filed with the  Commission  as an  exhibit to the  Registrant's
Registration  Statement on Form S-1  declared  effective on April 11, 1996 (File
No. 33-31482) and incorporated herein by reference.

(2)  Previously filed as an exhibit to the  Registrant's  Current Report on Form
8-K  filed on July 20,  1999  (File  No.  0-27886)  and  incorporated  herein by
reference.


         (b) Financial  statement  schedules are omitted because the information
called for is not required or is shown either in the financial statements or the
notes thereto.

                                      II-4

<PAGE>


                                   SIGNATURES

         Pursuant to the  requirements  of the  Securities  Act, the  Registrant
certifies  that it has  reasonable  grounds to believe that it meets all for the
requirements  for  filing  on Form S-3 and has  duly  caused  this  Registration
Statement  to be  signed  on its  behalf  by  the  undersigned,  thereunto  duly
authorized,  in the City of Santa Clara, State of California,  on the 8th day of
September 1999.


                                      WORLDTALK COMMUNICATIONS CORPORATION

                                      By: /s/ James Heisch
                                          --------------------------------------
                                          James Heisch
                                          President and Chief Financial Officer


                                POWER OF ATTORNEY

         KNOW ALL BY THESE PRESENTS that each individual whose signature appears
below  constitutes  and appoints Paul Hilal and James Heisch,  and each of them,
his attorneys-in-fact  and agents, each with the power of substitution,  for him
and in his name, place and stead, in any and all capacities, to sign any and all
amendments (including post-effective amendments) to this Registration Statement,
and to sign any  registration  statement for the same  offering  covered by this
Registration  Statement  that is to be  effective  upon filing  pursuant to Rule
462(b)  promulgated  under the Securities  Act of 1933,  and all  post-effective
amendments  thereto,  and to file the same,  with all  exhibits  thereto and all
documents in connection therewith,  with the Securities and Exchange Commission,
granting unto said  attorneys-in-fact  and agents,  and each of them, full power
and  authority  to do and  perform  each and every act and thing  requisite  and
necessary  to be done in and about the  premises,  as fully to all  intents  and
purposes as he might or could do in person,  hereby ratifying and confirming all
that  said  attorneys-in-fact  and  agents  or any  of  them,  or  his or  their
substitute or substitutes, may lawfully do or cause to be done by virtue hereof.

<TABLE>
         Pursuant to the  requirements of the Securities Act, this  Registration
Statement has been signed by the following  persons in the capacities and on the
dates indicated.

<CAPTION>
Signature                                      Title                                      Date
- ---------                                      -----                                      ----
<S>                                         <C>                                       <C>
Principal Executive Officer:

/s/ James Heisch                            President                                 September 8, 1999
- --------------------------------
James Heisch


Principal Financial and
Principal Accounting Officer:

s/s James Heisch                            Vice President, Finance, Chief            September 8, 1999
- --------------------------------            Financial Officer and Secretary
James Heisch

Directors:

/s/ David J. Cowan                          Director                                  September 8, 1999
- --------------------------------
David J. Cowan

/s/ Paul Hilal                              Director                                  September 8, 1999
- --------------------------------
Paul Hilal

/s/ Max D. Hopper                           Director                                  September 8, 1999
- --------------------------------
Max D. Hopper

/s/ Anthony Sun                             Director                                  September 8, 1999
- --------------------------------
Anthony Sun

/s/ Wade Woodson                            Director                                  September 8, 1999
- --------------------------------
Wade Woodson
</TABLE>

                                             II-5

<PAGE>


                                  EXHIBIT INDEX


   Exhibit
   Number                           Exhibit Title
   ------                           -------------

    3.01     Registrant's Certificate of Incorporation. (1)

    3.02     Registrant's Certificate of Designation. (1)

    3.03     Registrant's Certificate of Elimination. (1)

    4.02     Form of Specimen Common Stock Certificate.(1)

    5.01     Opinion of Fenwick & West LLP regarding  legality of the securities
             being registered.

   23.01     Consent of Fenwick & West LLP (included in Exhibit 5.01).

   23.02     Consent of KPMG LLP, Independent Auditors.

   24.01     Power of Attorney (see Page II-6).

   99.01     Securities Purchase Agreement entered into as of July 7, 1999 among
             the  Registrant and the parties listed on the Schedule of Investors
             attached thereto, with form of Escrow Agreement attached. (2)

   99.02     Registration  Rights  Agreement  entered into on July 7, 1999 among
             the Registrant and the Investors. (2)

   99.03     Form of Warrant issued as of July 7, 1999 to the Investors. (2)

- ----------------
(1)  Previously  filed with the  Commission  as an  exhibit to the  Registrant's
Registration  Statement on Form S-1  declared  effective on April 11, 1996 (File
No. 33-31482) and incorporated herein by reference.

(2) Previously  filed as an exhibit to the  Registrant's  Current Report on Form
8-K  filed on July 20,  1999  (File  No.  0-27886)  and  incorporated  herein by
reference.

                                      II-6




                                                                    EXHIBIT 5.01


                                September 8, 1999


Worldtalk Communications Corporation
5155 Old Ironsides Drive
Santa Clara, California, 95054

Gentlemen/Ladies:

         At your request,  we have examined the  Registration  Statement on Form
S-3 (the  "Registration  Statement")  to be filed by you with the Securities and
Exchange  Commission  (the  "Commission")  on or about  September  8,  1999,  in
connection with the  registration  under the Securities Act of 1933, as amended,
of an aggregate of 5,720,735  shares of your common stock (the "Stock") and will
be sold by certain selling stockholders (the "Selling Stockholders").  The Stock
consists  of  4,054,069  shares of common  stock that are  presently  issued and
outstanding and 1,666,666 shares of common stock that are issuable upon exercise
of outstanding warrants held by the Selling Stockholders (the "Warrants").

         In rendering this opinion, we have examined the following:

         (1)   your  registration  statement on Form S-1 (File Number  33-31482)
               filed with and declared  effective by the Commission on April 11,
               1996, together with the Exhibits filed as a part thereof;

         (2)   your  registration  statement on Form 8-A (File  number  0-27886)
               filed  with  the  Commission  on  March  4,  1996,  and  declared
               effective on April 11, 1996;

         (3)   the Registration Statement,  together with the Exhibits filed, as
               a part thereof or incorporated therein by reference;

         (4)   the  Prospectuses  prepared in connection  with the  Registration
               Statement;

         (5)   the  minutes of meetings  and  actions by written  consent of the
               stockholders  and Board of Directors  that are  contained in your
               minute books that are in our  possession  and the minute books of
               Worldtalk  Corporation,  a California corporation, with which you
               were merged;

         (6)   your stock records that you have provided to us  (consisting of a
               certificate from your transfer agent verifying the number of your
               issued and outstanding shares of capital stock as of September 7,
               1999, and a list of option and warrant  holders  respecting  your
               capital  and of any  rights to  purchase  capital  stock that was
               prepared by you and dated September 7, 1999, verifying the number
               of such issued and outstanding securities);

         (7)   a Management  Certificate  addressed to us and dated of even date
               herewith  executed by you  containing  certain  factual and other
               representations;

         (8)   the various stock purchase and other  agreements  under which the
               Selling  Stockholders  acquired  the Stock,  or will  acquire the
               Stock,  to be  sold  by them  as  described  in the  Registration
               Statement; and



<PAGE>


         (9)   Selling Stockholder  Questionnaires dated various dates in August
               and  September   1999   completed  and  signed  by  each  Selling
               Stockholder.

         By  telephone  call to the  offices  of the  Commission,  we have  also
confirmed the continued  effectiveness  of  Worldtalk's  registration  under the
Securities Exchange Act of 1934, as amended (the "Exchange Act"), and the timely
filing by you of all reports  required to be filed by you  pursuant to Rules 13,
14 and 15 promulgated under the Exchange Act.

         In our  examination of documents for purposes of this opinion,  we have
assumed,  and express no opinion as to, the  genuineness  of all  signatures  on
original documents, the authenticity and completeness of all documents submitted
to us as  originals,  the  conformity  to  originals  and  completeness  of  all
documents  submitted to us as copies,  the legal capacity of all natural persons
executing the same,  the lack of any  undisclosed  terminations,  modifications,
waivers or amendments to any documents reviewed by us and the due authorization,
execution and delivery of all documents where due  authorization,  execution and
delivery are prerequisites to the effectiveness thereof.

         As to matters of fact relevant to this  opinion,  we have relied solely
upon our  examination  of the  documents  referred to above and have assumed the
current  accuracy  and  completeness  of the  information  obtained  from public
officials  and  records   referred  to  above.   We  have  made  no  independent
investigation or other attempt to verify the accuracy of any of such information
or to determine the  existence or  non-existence  of any other factual  matters;
however,  we are not aware of any facts that would cause us to believe  that the
opinion expressed herein is not accurate.

         We are  admitted to  practice  law in the State of  California,  and we
express no opinion herein with respect to the  application or effect of the laws
of any jurisdiction other than the existing laws of the United States of America
and the State of  California  and  (without  reference  to case law or secondary
sources) the existing Delaware General Corporation Law.

         Based upon the  foregoing,  it is our  opinion  that (1) the  4,054,069
shares  of  Stock  to be  sold  by  the  Selling  Stockholders  pursuant  to the
Registration  Statement are validly issued, fully paid and nonassessable and (2)
the  1,666,666  shares  of Stock to be sold by the  Selling  Stockholders,  upon
exercise of the Warrants in  accordance  with the terms  thereof and pursuant to
the   Registration   Statement,   will  be  validly   issued,   fully  paid  and
nonassessable.

         We consent to the use of this opinion as an exhibit to the Registration
Statement  and  further  consent  to  all  references  to  us,  if  any,  in the
Registration  Statement,  the  Prospectus  constituting  a part  thereof and any
amendments thereto.

         This opinion  speaks only as of its date and we assume no obligation to
update this opinion  should  circumstances  change  after the date hereof.  This
opinion is  intended  solely for the your use as an exhibit to the  Registration
Statement for the purpose of the above sale of the Stock and is not to be relied
upon for any other purpose.


                                           Very truly yours,

                                           FENWICK & WEST LLP

                                           By: /s/ Gail E. Suniga
                                               ---------------------------------
                                               Gail E. Suniga, a Partner





                                                                   Exhibit 23.02


                         CONSENT OF INDEPENDENT AUDITORS

The Board of Directors
Worldtalk Communications Corporation:

We consent to  incorporation by reference herein of our report dated January 28,
1999 relating to the  consolidated  balance  sheets of Worldtalk  Communications
Corporation  and  subsidiary  as of December 31, 1998 and 1997,  and the related
consolidated statements of operations,  stockholders' equity (deficit), and cash
flows for each of the years in the  three-year  period ended  December 31, 1998,
and the  related  financial  statement  schedule,  which  report  appears in the
December  31,  1998,  annual  report  on Form 10-K of  Worldtalk  Communications
Corporation, and to the reference to our firm under the heading "Experts" in the
prospectus.

KPMG LLP

Mountain View, California
September 7, 1999




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