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Answered Thread: Forcing SMTP service to use a particular outbound IP?

Last post 06-18-2009 9:03 PM by steve schofield. 3 replies.

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  • 06-18-2009, 11:54 AM

    • e1ny
    • Top 50 Contributor
    • Joined on 12-10-2007, 9:50 PM
    • Posts 188

    Forcing SMTP service to use a particular outbound IP?

    Hi All: Is there any way to force the SMTP service to use a particular IP when sending mail? I've found that even if you bind the SMTP service to a particular IP, it will listen on that IP, but it won't actually send email from that IP (if you have more than one IP address bound to a NIC). It appears to use "any available" IP that isn't bound to a specific website or SMTP service.

    In IIS6, the behavior was similar but more predictable...no matter what IP you bound the SMTP service to, it would always send on the first IP bound to a NIC.

    Just wondering if I'm missing something obvious, or if there's a registry hack or something that can force SMTP to a particular IP?

    The reason I'm asking is because on a server with multiple SMTP services, each bound to a particular domain name/IP, when the receiving server does a reverse-lookup of the IP of the SMTP service, it will return a PTR name that is not the same as the EHLO (for a different domain entirely), and while there's nothing in the RFCs that says that's a problem, a lot of anti-spam devices will misinterpret that as a trojaned machine and block mail, or increase it's spam score. 

    I've found it increasingly difficult to prevent large ISPs from blocking mail when this happens. 

  • 06-18-2009, 7:42 PM In reply to

    Re: Forcing SMTP service to use a particular outbound IP?

    Good luck.  :) I never found a way.  I would have a single ip address on the smtp server, if possible.  Or use another 3rd party mail server instead of the built SMTP server such smartermail (www.smartertools.com)

     

    Steve Schofield
    Windows Server MVP - IIS
    http://weblogs.asp.net/steveschofield


    http://www.IISLogs.com
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  • 06-18-2009, 7:57 PM In reply to

    • e1ny
    • Top 50 Contributor
    • Joined on 12-10-2007, 9:50 PM
    • Posts 188

    Re: Forcing SMTP service to use a particular outbound IP?

    aw c'mon steve...that's the best you can do? where is your magic wand??? oh well...I will just have to keep fighting with comcast, aohell et al. at least comcast will remove you from their blocklist if you set the outbound connections-per-domain from "100" to "2"...can't say I blame them really!
  • 06-18-2009, 9:03 PM In reply to

    Answered Re: Forcing SMTP service to use a particular outbound IP?

    Sorry dude!  I'm only human. In a prior life, we used SMTP as part of windows and ran into this vary issue.  We uses smartermail and was able to bind to a specific ip address.  One thing you could try to change how SMTP service listens on all ips by default and assigned a specific ip address.  By default 0.0.0.0:25

    http://support.microsoft.com/kb/259349

    http://forums.iis.net/t/1088691.aspx

    Guess there might be a alternative.

    Steve Schofield
    Windows Server MVP - IIS
    http://weblogs.asp.net/steveschofield


    http://www.IISLogs.com
    Log archival solution
    Install, Configure, Forget
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