Home > Ask the Microsoft Exchange Experts > David Sengupta: Server Administration Questions & Answers > Cisco PIX firewall causing Exchange connectivity problems
Ask The Exchange Expert: Questions & Answers
EMAIL THIS

Cisco PIX firewall causing Exchange connectivity problems

David Sengupta EXPERT RESPONSE FROM: David Sengupta

Pose a Question
Other Exchange Categories
Meet all Exchange Experts
Become an Expert for this site


Exchange Server tips, tutorials and expert advice
Digg This!    StumbleUpon Toolbar StumbleUpon    Bookmark with Delicious Del.icio.us    Add to Google


>
QUESTION POSED ON: 18 January 2006
I'm running Exchange 5.5, and a certain host (EXTRANET2) needs to send mail out via SMTP. My IMC/SMTP servers are HOCON01 and ZABRYH02. Both are configured to allow SMTP connections from EXTRANET2.

When testing for connectivity, I start a telnet session from EXTRANET2 to HOCON01 on port 25, and instead of receiving the usual greeting as expected:

220 zabryh02.medscheme.com ESMTP Server (Microsoft Exchange Internet Mail Service 5.5.2657.72)

I get an apparently malformed greeting message:

220 *****0**********************************************************************
*****2*************

It seems like the connection is made, since it was not rejected, but no SMTP functionality is available. It does the same thing whether I'm connecting to HOCON01 or ZABRYH01. Other hosts can connect to HOCON01 and ZABRYH02 successfully.

EXTRANET2 is running Windows 2003 Enterprise Edition SP1 and HOCON01 and ZABRYH02 Windows 2000 Standard Edition SP4.

Do you have any ideas?



Digg This!    StumbleUpon Toolbar StumbleUpon    Bookmark with Delicious Del.icio.us    Add to Google



RELATED CONTENT
David Sengupta: Server Administration
Changing email address formats in Exchange Server 2003
Should you remove .STM files from Exchange Server 2003?
Exchange users receiving email addressed to legacy users
Pushing a public calendar out from a private Exchange account
Import and export .PST files in Exchange Server 2007
Editing Exchange Server public folder permissions
Search and index Microsoft Outlook 2007 public folders
Troubleshooting Microsoft Exchange Server Event ID error 6009
Can't delete old Microsoft Outlook public folders
Can't create mailboxes after virtualizing Microsoft Exchange Server

Legacy Microsoft Exchange Servers
Troubleshooting Outlook calendar errors on a BlackBerry device
How to move Exchange 2000 to new server hardware
Migrating mailboxes from Exchange Server 5.5 to Windows SBS 2003
Remove Exchange 5.5 servers from a mixed mode Exchange environment
Error 1053: Exchange System Attendant service could not start
Solve server problems with the Exchange Troubleshooting Assistant tool
Best approaches for upgrading Exchange 5.5 to Exchange 2000 or 2003
Move mailboxes to Exchange 2007 after Windows upgrade
Third-party tools that modify NDRs for oversized email
IP address changes for an Exchange 2000 recovery server
Legacy Microsoft Exchange Servers Research

ISA Server and Firewalls for Microsoft Exchange Server
Top 5 Exchange mobile tips of 2008
Microsoft Exchange Server security dos and don'ts
Windows SBS and Exchange Server security configuration best practices
Why Exchange ActiveSync fails with NAT firewalls
Deploying ISA Server as a firewall for Exchange Server mobile devices
Adjust your firewall to avoid Exchange 2007 Direct Push failures
OWA stops working from external network connection
Enhance OWA logon security using Microsoft ISA Server
Firewall problems with Exchange Server 2007 email attachments
How and why to disable certain ESMTP verbs

RELATED GLOSSARY TERMS
Terms from Whatis.com − the technology online dictionary
E2K  (SearchExchange.com)

RELATED RESOURCES
2020software.com, trial software downloads for accounting software, ERP software, CRM software and business software systems
Search Bitpipe.com for the latest white papers and business webcasts
Whatis.com, the online computer dictionary


Yes, I have seen this many times over the years. This looks to me to be a classic Cisco PIX firewall SMTP banner, because the Mailguard feature is enabled on the firewall.

Have a look at Microsoft Knowledge Base article 320027, Cannot send or receive e-mail messages behind a Cisco PIX firewall, which describes the behavior you're seeing. Follow the instructions to turn off Mailguard and your problem will go away.


Do you have comments on this Ask the Expert Q&A? Let us know.
Related information from SearchExchange.com:

  • Expert Advice: Error: 'You do not have permission to send to this recipient'
  • Tip: Firewall policies and SMTP line lengths
  • Resource Center: Firewall tips and resources




  • Search and Browse the Expert Answer Center
    Search and browse more than 25,000 question and answer pairs from more than 250 TechTarget industry experts.
    Browse our Expert Advice



    Outlook Web Access (OWA) Tips and Advice
    HomeNewsTopicsITKnowledge ExchangeTipsAsk the ExpertsMultimediaWhite PapersIT Downloads
    About Us  |  Contact Us  |  For Advertisers  |  For Business Partners  |  Site Index  |  RSS
    SEARCH 
    TechTarget provides technology professionals with the information they need to perform their jobs - from developing strategy, to making cost-effective purchase decisions and managing their organizations' technology projects - with its network of technology-specific websites, events and online magazines.

    TechTarget Corporate Web Site  |  Media Kits  |  Site Map




    All Rights Reserved, Copyright 2004 - 2009, TechTarget | Read our Privacy Policy
      TechTarget - The IT Media ROI Experts