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GFI White Paper

          GFI MailSecurity™
        deployment strategies
Which operating mode(s) to use in your network environment

   GFI MailSecurity can be deployed as an SMTP gateway
   or as a VS API version for Microsoft Exchange Server™.
     This white paper describes each operating mode
         and helps you decide which to deploy and
              whether you should deploy both.
Contents
                  Introduction                                                          3
                  Why use both VS API and SMTP gateway modes?                           3
                  About GFI MailSecurity SMTP gateway mode                              3
                  GFI MailSecurity VS API Exchange mode                                 3
                  Limitations of using the VS API Exchange mode                         4
                  Comparison between SMTP Gateway mode and VS API mode                  4
                  How to deploy GFI MailSecurity                                        5
                  GFI MailEssentials and GFI MailSecurity running on the same machine   8
                  About GFI®                                                            8




GFI MailSecurity deployment strategies                                                      2
Introduction
GFI MailSecurity can be deployed in two operating modes: Either as an SMTP gateway or as a VS API version
for Microsoft Exchange Server. It can be used in three ways, either by using one of these modes or by using
both in tandem. This paper describes the GFI MailSecurity operating modes in detail and helps you choose
the best way to deploy GFI MailSecurity on your network.

Why use both VS API and SMTP gateway modes?
GFI MailSecurity is an email content security package that supports both an SMTP gateway mode and a VS
API mode. For optimum security, we recommend deploying both. This is because both operating modes have
unique capabilities that enable you to ensure better security for your network and mail server.
In SMTP gateway mode, GFI MailSecurity checks all inbound and outbound mail before this reaches your
mail server. For GFI MailSecurity to do this, you must install it in front of your mail server. In VS API mode, GFI
MailSecurity is installed on your Exchange Server and checks inbound, outbound and internal mail, using the
Microsoft VS API interface.
If possible, you should deploy both versions. For administration and performance reasons, it is better to
perform the more complex and time-intensive checks at the gateway level. If you were to apply those rules
to internal mail, you would end up having to moderate a lot of mail. However, the VS API mode should still
be deployed on the Exchange Server, in order to stop a virus outbreak spreading (that could have entered
the network via floppy, CD, web or notebook) or in order to monitor and/or stop internal users using email
exploits to steal data. You can also use it to prevent unauthorized users from sending executable attachments,
which they might use to gain information from users who have more rights on the network.

About GFI MailSecurity SMTP gateway mode
If you wish to install GFI MailSecurity at the perimeter of your network, or if you do not have Microsoft
Exchange Server, you must install GFI MailSecurity in SMTP gateway mode.
In SMTP gateway mode, GFI MailSecurity checks all inbound and outbound mail before this reaches your
mail server. To do this, GFI MailSecurity must be the first to receive all mails destined for your mail server
and it must be the last “stop” for outbound mail, i.e., mails destined for the Internet. For this to happen, GFI
MailSecurity must act as a gateway for all email. This set-up is also known as “Smart host” or “Mail relay” server.
Effectively, GFI MailSecurity will act as a mail relay server.

GFI MailSecurity VS API Exchange mode
If you have Microsoft Exchange Server, GFI MailSecurity can integrate with Exchange via the Microsoft Virus
Scanning API (VS API).
What is VS API (Exchange Virus Scanning API) and why use it?
Microsoft Exchange Server provides a virus scanning API that is implemented at a very low-level in the
Exchange store. This allows a virus scanning application to run with high performance and guarantees that
the message will be scanned before any client can access a message or attachment. This low-level access
facilitates the elimination of viruses such as the Melissa virus.
In addition, VS API reduces scalability issues that can arise when a particular server has a large number
of users/mailboxes. VS API’s real-time scan allows messages and attachments to be scanned once before
delivery, rather than multiple times determined by the number of mailboxes the message is delivered to. This
single-instance scanning also helps prevent messages from being rescanned when a message is copied. For
more information about VS API, see http://support.microsoft.com/default.aspx?scid=kb;EN-US;q285667.




GFI MailSecurity deployment strategies                                                                                3
Limitations of using the VS API Exchange mode
Although VS API is a recommended way to perform content checking and antivirus on Exchange Server, there
are a number of limitations that you should be aware of as a system administrator:
»»   The Virus Scanning API only scans information stores. That means that if you have installed GFI
     MailSecurity for Exchange on a front-end server, for example, internal mail will not be scanned, because
     mail is not being stored on the front-end server. Only incoming and outgoing emails will be scanned by
     GFI MailSecurity. You need to be more careful with applying attachment rules since these might affect
     internal traffic; attachment rules that are too stringent can result in too much quarantined mail. Also, MAPI
     applications running on Exchange might be using .vbs or .exe files.
»»   Outgoing mails that have been approved need to be resent by the user. For example, if an executable
     is quarantined and approved, the user will receive a message saying that he/she has 24 hours to resend
     that executable. The reason for this is that the recipient of the message is not always known with 100%
     certainty in VS API mode.
»»   In VS API mode, mail is processed in parts. The Exchange VS API interface passes mails to GFI MailSecurity
     per message part, i.e., the body, attachment 1, attachment 2, etc. This means that message parts are
     quarantined, not whole messages. Therefore, all rules are applied to a message part. For example, you
     cannot delete an entire mail if it has a particular content, but only the message part containing that
     content.
»»   In VS API mode, some performance decrease will occur in mail delivery. This is inevitable as all mail has to
     be checked before the user accesses it. Typically, the delay is approximately 1 second or less, but a mail
     with a large 15 megabyte attachment, for example, might take more time to scan. Every VS API-based
     antivirus solution will suffer from this performance decrease, although of course the less checks that are
     done, the less performance decrease there will be.

Comparison between SMTP Gateway mode and VS API mode
                                                                            SMTP gateway                              VS API
 Scans internal mail                                                        No                                        Yes
 Scans inbound/outbound mail                                                Yes                                       Yes
 Requires Windows 2000/2003/2008                                            Yes                                       Yes
 Requires Active Directory                                                  No                                        Yes
 Requires Exchange 2000/2003/2007                                           No                                        Yes
 Mail processed in parts                                                    No                                        Yes
 Can run on same machine as
                                                                            Yes                                       Yes
 GFI MailEssentials
 Can run if you have Exchange 5.5                                           Yes                                       No
 Can run if you have Notes or SMTP server                                   Yes                                       No
 Can run in DMZ or as mail relay                                            Yes                                       No
 Ticketing system needed*                                                   No                                        Yes
 100% Inbound/internal mail detection**                                     Yes                                       No
*SMTP gateway version has more information about the email and can therefore quarantine outbound mail without the need for a ticketing system.

**SMTP gateway version has more information about the email and can therefore better determine if it is an inbound or an outbound mail.




GFI MailSecurity deployment strategies                                                                                                           4
How to deploy GFI MailSecurity
Deployment option 1




If you have a smaller Exchange network and do not want to have a separate mail relay in the DMZ, use VS API
mode only; or if you prefer Gateway mode only.




GFI MailSecurity deployment strategies                                                                        5
Deployment option 2




If you do not have Exchange Server, deploy GFI MailSecurity in SMTP Gateway mode. So if you have Exchange
5.5, Lotus Notes or another SMTP/POP3 server, you must use SMTP gateway mode.




GFI MailSecurity deployment strategies                                                                  6
Deployment option 3




If you have a larger network with one or more Exchange Servers, we recommend you deploy GFI MailSecurity
both on the Exchange 2000/2003 machine in VS API mode, as well as at the perimeter of your network in
SMTP Gateway mode. This is the ideal deployment scenario: the main advantage of this deployment is that
you can have stricter rules on inbound and outbound mail and less strict rules on internal mail.




GFI MailSecurity deployment strategies                                                                 7
GFI MailEssentials and GFI MailSecurity running on the same machine
GFI MailEssentials and GFI MailSecurity are companion products and can easily run on the same machine.
GFI MailEssentials adds essential email tools to your Exchange Server including anti-spam, disclaimers, mail
archiving, Internet mail reporting, server-based auto replies and POP3 downloading. Special bundle pricing
applies when GFI MailEssentials and GFI MailSecurity are purchased together.

About GFI
GFI Software provides web and mail security, archiving, backup and fax, networking and security software
and hosted IT solutions for small to medium-sized enterprises (SMEs) via an extensive global partner
community. GFI products are available either as on-premise solutions, in the cloud or as a hybrid of both
delivery models. With award-winning technology, a competitive pricing strategy, and a strong focus on the
unique requirements of SMEs, GFI satisfies the IT needs of organizations on a global scale. The company has
offices in the United States (North Carolina, California and Florida), UK (London and Dundee), Austria, Australia,
Malta, Hong Kong, Philippines and Romania, which together support hundreds of thousands of installations
worldwide. GFI is a channel-focused company with thousands of partners throughout the world and is also a
Microsoft Gold Certified Partner.
More information about GFI can be found at http://www.gfi.com.




                                                                                                                 8
USA,»CANADA»AND»CENTRAL»AND»SOUTH»AMERICA




                                                                                                                                                                                               GFI 1019 may11
15300 Weston Parkway, Suite 104, Cary, NC 27513, USA
Telephone: +1 (888) 243-4329
Fax: +1 (919) 379-3402
ussales@gfi.com



UK»AND»REPUBLIC»OF»IRELAND
Magna House, 18-32 London Road, Staines, Middlesex, TW18 4BP, UK
Telephone: +44 (0) 870 770 5370
Fax: +44 (0) 870 770 5377
sales@gfi.co.uk



EUROPE,»MIDDLE»EAST»AND»AFRICA
GFI House, San Andrea Street, San Gwann, SGN 1612, Malta
Telephone: +356 2205 2000
Fax: +356 2138 2419
sales@gfi.com



AUSTRALIA»AND»NEW»ZEALAND
83 King William Road, Unley 5061, South Australia
Telephone: +61 8 8273 3000
Fax: +61 8 8273 3099
sales@gfiap.com




Disclaimer

© 2011. GFI Software. All rights reserved. All product and company names herein may be trademarks of their respective owners.

The information and content in this document is provided for informational purposes only and is provided “as is” with no warranty of any kind, either express or implied, including but
not limited to the implied warranties of merchantability, fitness for a particular purpose, and non-infringement. GFI Software is not liable for any damages, including any consequential
damages, of any kind that may result from the use of this document. The information is obtained from publicly available sources. Though reasonable effort has been made to ensure the
accuracy of the data provided, GFI makes no claim, promise or guarantee about the completeness, accuracy, recency or adequacy of information and is not responsible for misprints, out-
of-date information, or errors. GFI makes no warranty, express or implied, and assumes no legal liability or responsibility for the accuracy or completeness of any information contained in
this document.

If you believe there are any factual errors in this document, please contact us and we will review your concerns as soon as practical.

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GFI MailSecurity's Deployment Strategies

  • 1. GFI White Paper GFI MailSecurity™ deployment strategies Which operating mode(s) to use in your network environment GFI MailSecurity can be deployed as an SMTP gateway or as a VS API version for Microsoft Exchange Server™. This white paper describes each operating mode and helps you decide which to deploy and whether you should deploy both.
  • 2. Contents Introduction 3 Why use both VS API and SMTP gateway modes? 3 About GFI MailSecurity SMTP gateway mode 3 GFI MailSecurity VS API Exchange mode 3 Limitations of using the VS API Exchange mode 4 Comparison between SMTP Gateway mode and VS API mode 4 How to deploy GFI MailSecurity 5 GFI MailEssentials and GFI MailSecurity running on the same machine 8 About GFI® 8 GFI MailSecurity deployment strategies 2
  • 3. Introduction GFI MailSecurity can be deployed in two operating modes: Either as an SMTP gateway or as a VS API version for Microsoft Exchange Server. It can be used in three ways, either by using one of these modes or by using both in tandem. This paper describes the GFI MailSecurity operating modes in detail and helps you choose the best way to deploy GFI MailSecurity on your network. Why use both VS API and SMTP gateway modes? GFI MailSecurity is an email content security package that supports both an SMTP gateway mode and a VS API mode. For optimum security, we recommend deploying both. This is because both operating modes have unique capabilities that enable you to ensure better security for your network and mail server. In SMTP gateway mode, GFI MailSecurity checks all inbound and outbound mail before this reaches your mail server. For GFI MailSecurity to do this, you must install it in front of your mail server. In VS API mode, GFI MailSecurity is installed on your Exchange Server and checks inbound, outbound and internal mail, using the Microsoft VS API interface. If possible, you should deploy both versions. For administration and performance reasons, it is better to perform the more complex and time-intensive checks at the gateway level. If you were to apply those rules to internal mail, you would end up having to moderate a lot of mail. However, the VS API mode should still be deployed on the Exchange Server, in order to stop a virus outbreak spreading (that could have entered the network via floppy, CD, web or notebook) or in order to monitor and/or stop internal users using email exploits to steal data. You can also use it to prevent unauthorized users from sending executable attachments, which they might use to gain information from users who have more rights on the network. About GFI MailSecurity SMTP gateway mode If you wish to install GFI MailSecurity at the perimeter of your network, or if you do not have Microsoft Exchange Server, you must install GFI MailSecurity in SMTP gateway mode. In SMTP gateway mode, GFI MailSecurity checks all inbound and outbound mail before this reaches your mail server. To do this, GFI MailSecurity must be the first to receive all mails destined for your mail server and it must be the last “stop” for outbound mail, i.e., mails destined for the Internet. For this to happen, GFI MailSecurity must act as a gateway for all email. This set-up is also known as “Smart host” or “Mail relay” server. Effectively, GFI MailSecurity will act as a mail relay server. GFI MailSecurity VS API Exchange mode If you have Microsoft Exchange Server, GFI MailSecurity can integrate with Exchange via the Microsoft Virus Scanning API (VS API). What is VS API (Exchange Virus Scanning API) and why use it? Microsoft Exchange Server provides a virus scanning API that is implemented at a very low-level in the Exchange store. This allows a virus scanning application to run with high performance and guarantees that the message will be scanned before any client can access a message or attachment. This low-level access facilitates the elimination of viruses such as the Melissa virus. In addition, VS API reduces scalability issues that can arise when a particular server has a large number of users/mailboxes. VS API’s real-time scan allows messages and attachments to be scanned once before delivery, rather than multiple times determined by the number of mailboxes the message is delivered to. This single-instance scanning also helps prevent messages from being rescanned when a message is copied. For more information about VS API, see http://support.microsoft.com/default.aspx?scid=kb;EN-US;q285667. GFI MailSecurity deployment strategies 3
  • 4. Limitations of using the VS API Exchange mode Although VS API is a recommended way to perform content checking and antivirus on Exchange Server, there are a number of limitations that you should be aware of as a system administrator: »» The Virus Scanning API only scans information stores. That means that if you have installed GFI MailSecurity for Exchange on a front-end server, for example, internal mail will not be scanned, because mail is not being stored on the front-end server. Only incoming and outgoing emails will be scanned by GFI MailSecurity. You need to be more careful with applying attachment rules since these might affect internal traffic; attachment rules that are too stringent can result in too much quarantined mail. Also, MAPI applications running on Exchange might be using .vbs or .exe files. »» Outgoing mails that have been approved need to be resent by the user. For example, if an executable is quarantined and approved, the user will receive a message saying that he/she has 24 hours to resend that executable. The reason for this is that the recipient of the message is not always known with 100% certainty in VS API mode. »» In VS API mode, mail is processed in parts. The Exchange VS API interface passes mails to GFI MailSecurity per message part, i.e., the body, attachment 1, attachment 2, etc. This means that message parts are quarantined, not whole messages. Therefore, all rules are applied to a message part. For example, you cannot delete an entire mail if it has a particular content, but only the message part containing that content. »» In VS API mode, some performance decrease will occur in mail delivery. This is inevitable as all mail has to be checked before the user accesses it. Typically, the delay is approximately 1 second or less, but a mail with a large 15 megabyte attachment, for example, might take more time to scan. Every VS API-based antivirus solution will suffer from this performance decrease, although of course the less checks that are done, the less performance decrease there will be. Comparison between SMTP Gateway mode and VS API mode SMTP gateway VS API Scans internal mail No Yes Scans inbound/outbound mail Yes Yes Requires Windows 2000/2003/2008 Yes Yes Requires Active Directory No Yes Requires Exchange 2000/2003/2007 No Yes Mail processed in parts No Yes Can run on same machine as Yes Yes GFI MailEssentials Can run if you have Exchange 5.5 Yes No Can run if you have Notes or SMTP server Yes No Can run in DMZ or as mail relay Yes No Ticketing system needed* No Yes 100% Inbound/internal mail detection** Yes No *SMTP gateway version has more information about the email and can therefore quarantine outbound mail without the need for a ticketing system. **SMTP gateway version has more information about the email and can therefore better determine if it is an inbound or an outbound mail. GFI MailSecurity deployment strategies 4
  • 5. How to deploy GFI MailSecurity Deployment option 1 If you have a smaller Exchange network and do not want to have a separate mail relay in the DMZ, use VS API mode only; or if you prefer Gateway mode only. GFI MailSecurity deployment strategies 5
  • 6. Deployment option 2 If you do not have Exchange Server, deploy GFI MailSecurity in SMTP Gateway mode. So if you have Exchange 5.5, Lotus Notes or another SMTP/POP3 server, you must use SMTP gateway mode. GFI MailSecurity deployment strategies 6
  • 7. Deployment option 3 If you have a larger network with one or more Exchange Servers, we recommend you deploy GFI MailSecurity both on the Exchange 2000/2003 machine in VS API mode, as well as at the perimeter of your network in SMTP Gateway mode. This is the ideal deployment scenario: the main advantage of this deployment is that you can have stricter rules on inbound and outbound mail and less strict rules on internal mail. GFI MailSecurity deployment strategies 7
  • 8. GFI MailEssentials and GFI MailSecurity running on the same machine GFI MailEssentials and GFI MailSecurity are companion products and can easily run on the same machine. GFI MailEssentials adds essential email tools to your Exchange Server including anti-spam, disclaimers, mail archiving, Internet mail reporting, server-based auto replies and POP3 downloading. Special bundle pricing applies when GFI MailEssentials and GFI MailSecurity are purchased together. About GFI GFI Software provides web and mail security, archiving, backup and fax, networking and security software and hosted IT solutions for small to medium-sized enterprises (SMEs) via an extensive global partner community. GFI products are available either as on-premise solutions, in the cloud or as a hybrid of both delivery models. With award-winning technology, a competitive pricing strategy, and a strong focus on the unique requirements of SMEs, GFI satisfies the IT needs of organizations on a global scale. The company has offices in the United States (North Carolina, California and Florida), UK (London and Dundee), Austria, Australia, Malta, Hong Kong, Philippines and Romania, which together support hundreds of thousands of installations worldwide. GFI is a channel-focused company with thousands of partners throughout the world and is also a Microsoft Gold Certified Partner. More information about GFI can be found at http://www.gfi.com. 8
  • 9. USA,»CANADA»AND»CENTRAL»AND»SOUTH»AMERICA GFI 1019 may11 15300 Weston Parkway, Suite 104, Cary, NC 27513, USA Telephone: +1 (888) 243-4329 Fax: +1 (919) 379-3402 ussales@gfi.com UK»AND»REPUBLIC»OF»IRELAND Magna House, 18-32 London Road, Staines, Middlesex, TW18 4BP, UK Telephone: +44 (0) 870 770 5370 Fax: +44 (0) 870 770 5377 sales@gfi.co.uk EUROPE,»MIDDLE»EAST»AND»AFRICA GFI House, San Andrea Street, San Gwann, SGN 1612, Malta Telephone: +356 2205 2000 Fax: +356 2138 2419 sales@gfi.com AUSTRALIA»AND»NEW»ZEALAND 83 King William Road, Unley 5061, South Australia Telephone: +61 8 8273 3000 Fax: +61 8 8273 3099 sales@gfiap.com Disclaimer © 2011. GFI Software. All rights reserved. All product and company names herein may be trademarks of their respective owners. The information and content in this document is provided for informational purposes only and is provided “as is” with no warranty of any kind, either express or implied, including but not limited to the implied warranties of merchantability, fitness for a particular purpose, and non-infringement. GFI Software is not liable for any damages, including any consequential damages, of any kind that may result from the use of this document. The information is obtained from publicly available sources. Though reasonable effort has been made to ensure the accuracy of the data provided, GFI makes no claim, promise or guarantee about the completeness, accuracy, recency or adequacy of information and is not responsible for misprints, out- of-date information, or errors. GFI makes no warranty, express or implied, and assumes no legal liability or responsibility for the accuracy or completeness of any information contained in this document. If you believe there are any factual errors in this document, please contact us and we will review your concerns as soon as practical.