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SBS unable to send emails with attachments.

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  • SBS unable to send emails with attachments.

    Hi all,

    I have an issue with an SBS 2003 system. The system has been running fine for some time now, (around 12 months) with one exception:
    Users (there are 3 of them) are unable to send emails with attachments to a handful of addresses. (AOL, BT and another company's domain)

    I have confirmed over the months that:
    1> The recipients are not blocking these mails and the recipiantís domains etc are not blocking them either.
    2> The outbound serverís IP is not blacklisted
    3> The attachments fit the msg limits/attachment size limits etc
    4> The problem is present when routing email by both DNS and via an authenticated smart host on a diff. Port (, via port 2525).
    5> They can send emails without attachments successfully.

    The symptoms are:
    Outbound email sits in the outbound queue on the server for a period of time and then times out (user gets a delay notification then an NDR).

    When email is routed by DNS, the queue shows an entry per destination domain, when routed by smart host, it shows one entry (the smart host).

    I have used the same setup (SBS vs + Server hardware + Router + ISP combination) with other clients and had no issues.

    Any ideas?

  • #2
    Re: SBS unable to send emails with attachments.

    Lots of info, thanks.
    What does the NDR say?
    What AV/AS do you have on the Exchange?
    When you say 3 users, does that mean other users on the same SBS can send without issue to the same addresses?
    If one of these users logs onto a clean machine they haven't been on before does it still happen?

    Please read this before you post:

    Quis custodiet ipsos custodes?