Home > Microsoft Exchange Tips > Exchange Server Administration Tips > Firewall policies and SMTP line lengths
Exchange Tips:
EMAIL THIS
 TIPS & NEWSLETTERS TOPICS 

EXCHANGE SERVER ADMINISTRATION TIPS

Firewall policies and SMTP line lengths


Serdar Yegulalp
05.11.2005
Rating: -4.75- (out of 5)


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


VIEW MEMBER FEEDACK TO THIS TIP

Illegal line lengths in incoming e-mail are one of those subtle problems that aren't often noticed and can be difficult to diagnose.

The RFC for the SMTP standard expressly forbids having an e-mail line length (i.e., a string of characters terminated by a carriage return/line-feed pair) of more than 1,000 bytes. (This sort of formatting is often the hallmark of a buffer-overrun attack, which is why it's generally a good idea to block such messages.)

Spammers often disregard the 1,000-byte line-length limit. But, unfortunately, some perfectly legitimate (albeit misconfigured) e-mail handlers also sometimes disregard this limit. Conventional e-mail typically wraps at 72 lines, but this a holdover from the days of fixed-width 80-column displays and isn't being treated as an ironclad rule anymore.

E-mail that is badly-formatted in this fashion can lead to a peculiar situation where one group replies to e-mail from another group, only to have the reply rejected. Replies from all other organizations come through fine, but that particular group's replies get bounced.

As an administrator, you might blame Exchange for this problem (either on the sending or receiving end), but the real culprit may lie between the two servers: the SMTP proxy or firewall.

Many firewalls and proxies, including Microsoft's own ISA Server, monitor SMTP traffic, and will terminate an SMTP session if someone attempts to send a message with an unterminated line longer than 1,000 characters.

One way to get around this is to make the firewall's SMTP monitoring rules less restrictive (for instance, to terminate sessions at 2,000 lines) -- but the party sending the malformed e-mails needs to be the one to fix the problem. (You can find instructions on how to configure the maximum line length in ISA Server here.

Another way to work around this problem as a sender is to force all outgoing e-mail to be 8-bit MIME-encoded. This removes the line-length problem, since MIME encoding uses a standard line length in its data that is universally respected. However, older versions of Exchange (4.0 through 5.5) cannot handle 8-bit MIME, so this should only be used if you are confident that the majority of the e-mail you send will be readable.

About the author: Serdar Yegulalp is the editor of the Windows Power Users Newsletter and a regular contributor to SearchExchange.com.


MEMBER FEEDBACK TO THIS TIP

It was nice to find an article on this issue that I can point offending senders to when their email is rejected.

I think this line: "One way to get around this is to make the firewall's SMTP monitoring rules less restrictive (for instance, to terminate sessions at 2,000 lines)" …should read something like: "One way to get around this is to make the firewall's SMTP monitoring rules less restrictive (for instance, to terminate sessions at 2,000 characters/octets)."
—Dana D.


Do you have comments on this tip? Let us know.

Related information from SearchExchange.com:

  • Column: Should you use ISA Server as your Exchange firewall?
  • Topics Library: SMTP tips and expert advice
  • Topics Library: Firewalls

    Please let others know how useful this tip is via the rating scale below. Do you have a useful Exchange Server or Microsoft Outlook tip, timesaver or workaround to share? Submit it to our tip contest and you could win a prize.

    Rate this Tip
    To rate tips, you must be a member of SearchExchange.com.
    Register now to start rating these tips. Log in if you are already a member.


    Submit a Tip




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


    RELATED CONTENT
    Exchange Server Administration Tips
    Why are .PST files a security threat to Exchange Server mailboxes?
    EMS add-on tool generates graphical Exchange Server 2007 reports
    Third-party Exchange Server 2007 backup and restore tools
    Repairing damaged OWA virtual directories in Exchange Server 2003
    Exchange Server 2007 hardware planning for continuous replication
    Benefits of SAN-based storage in Microsoft Exchange Server 2007
    How to generate HTML reports with the Exchange Management Shell (EMS)
    Hosted Exchange Server adoption to infiltrate the enterprise
    Using ActiveSync without a front-end Exchange server
    Use the Exchange Management Shell Set command to block senders

    SMTP
    Reconfigure an existing Exchange Server user account for a new user
    Improve Exchange 2003 Internet connectivity, mail flow and performance
    Troubleshoot Exchange 2003 email that gets stuck in the SMTP queue
    Perform an SMTP Telnet to test an outgoing Exchange server connection
    A primer on SMTP and ESMTP servers and commands
    How to use SMTP queues to troubleshoot mail flow
    SMTP greylisting problem on Exchange Server 2003 SP2
    How to retrieve email from an SMTP server using POP3
    SMTP 550 relay error when sending large attachments
    Sending email to an Exchange distribution list containing SMTP and EX addresses

    ISA Server and Firewalls for Microsoft Exchange Server
    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
    Creating an ethical firewall in Exchange Server 2007
    Beware of firewalls that block Exchange Server's SMTP/POP3 communications
    How HTTP verbs can 'hang' Outlook Web Access

    RELATED GLOSSARY TERMS
    Terms from Whatis.com − the technology online dictionary
    SMTP  (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

    DISCLAIMER: Our Tips Exchange is a forum for you to share technical advice and expertise with your peers and to learn from other enterprise IT professionals. TechTarget provides the infrastructure to facilitate this sharing of information. However, we cannot guarantee the accuracy or validity of the material submitted. You agree that your use of the Ask The Expert services and your reliance on any questions, answers, information or other materials received through this Web site is at your own risk.

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

    TechTarget Corporate Web Site  |  Media Kits  |  Reprints  |  Site Map




    All Rights Reserved, Copyright 2004 - 2008, TechTarget | Read our Privacy Policy
      TechTarget - The IT Media ROI Experts