WORLDTALK COMMUNICATIONS CORP
424B3, 1999-10-12
PREPACKAGED SOFTWARE
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PROSPECTUS



                                5,720,735 SHARES

                      WORLDTALK COMMUNICATIONS CORPORATION

                                  COMMON STOCK

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

    The  selling  stockholders  identified  on page 15 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
16. 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 October 8,  1999,  the last sale price of the common  stock on the Nasdaq
National Market was $4.2813 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 October 11, 1999.


                                       1

<PAGE>

                               TABLE OF CONTENTS

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

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

Forward-Looking Statements ................................................   14

Use of Proceeds ...........................................................   14

Selling Stockholders ......................................................   15

Plan of Distribution ......................................................   16

Legal Matters .............................................................   18

Experts ...................................................................   18

Change in Management ......................................................   18

Documents Incorporated By Reference In This Prospectus ....................   18

Where You Can Find More Information .......................................   19


                                       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  and NetTalk  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:

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

    o   our distributor inventory levels;

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

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

    o   the mix of products we sell;

    o   the success of our WorldSecure products;

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

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

    o   trends in the computer industry;

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

    o   costs related to acquisitions of technology or businesses; and

    o   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.


                                       4

<PAGE>

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

    During the nine months  ended  September  30,  1999,  our stock price on the
Nasdaq  National  Market ranged from a high of $6.00 per share to a low of $2.25
per share.  At the close of market on September  30,  1999,  our stock price was
$4.1875 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:

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

    o   market acceptance of our WorldSecure products;

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

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

    o   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.


                                       5

<PAGE>


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:

    o   offer a broad range of policy management products;

    o   continue to enhance existing products and expand product offerings;

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

    o   respond promptly to new customer requirements;

    o   comply with evolving industry standards without delays in compliance;

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

    o   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.


                                       6

<PAGE>

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 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.


                                       7

<PAGE>

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:

    o   performance;

    o   functionality;

    o   scalability;

    o   customer support;

    o   breadth of product line;

    o   frequency of upgrades and updates;

    o   integration of products;

    o   manageability of products;

    o   brand name recognition; and

    o   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  than we do.
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 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 that 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


                                       8

<PAGE>

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
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


                                       9

<PAGE>

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 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:

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

    o   effectively integrate new employees into our operations; and

    o   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.

    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


                                       10

<PAGE>

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:

    o   result in the loss of our proprietary rights;

    o   subject us to significant liabilities;

    o   require us to seek licenses from third parties; or

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

    o   lengthy payment cycles;

    o   greater difficulty in accounts receivable collection;

    o   unexpected changes in regulatory requirements;


                                       11

<PAGE>

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

    o   tariffs and other trade barriers;

    o   export restrictions on encryption and other security products;

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

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

    o   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 products and limited  knowledge of the  information  provided by, or
representations   made  by,  these  agents  to  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 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.


                                       12

<PAGE>

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  third  parties'
businesses.  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.


                                       13

<PAGE>

    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  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.


                                       14

<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.

    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.
<TABLE>
<CAPTION>
                                                      Shares                                  Shares
                                                   Beneficially                            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>
(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.


                                       15

<PAGE>

(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 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


                                       16

<PAGE>

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,  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


                                       17

<PAGE>

filing fees,  printing expenses,  administrative  expenses and certain legal and
accounting fees. The 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 has
been 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)


                                       18

<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.


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