Exchange 2007 gmails with attachments not being received

Posted on 2011-10-24
Last Modified: 2012-05-12
I have clients server: Exchange 2007 SP3 / Rollup 5, with Trend Worry 7 Advanced
Within the past week - users have been complaining about extended delivery times of emails (inbound) with attachments.  Some taking several hours to deliver (inbound) - usually with a tiny attachmentt - less than 100kb.
I've spent hours troubleshooting this.
Emails from other exchange servers with attachments are delivered instantly.  I've recently updated to Rollup 5 - no change.  Disabled all Trend spam filtering - no change.  Disabled Exchange antispam content filters etc.
Added the users domain into approved senders - you name it - I've given it a go.
The only way to recreate the prooblem is to send an email from a gmail account - without attachement - it is delviered almost instantly - within millisecs.  however with an attachement - doesn't arrive at all.  I've CC the same email to our own setup - which is identical - yet the emails are delivered to our system.
Completely out of ideas??
: (

Question by:weryourit2
    LVL 14

    Expert Comment

    by:Shabarinath Ramadasan
    Would you be able to post the message header of one such delayed mail?
    Seems to be an issue with the Antispam filter which may be limiting the number of emails from a domain with low score.

    Author Comment

    There is no delayed message or NDR - it looks like the message simply vanishes.  
    I can not trace where the email with the attachment gets blocked - perhaps on google email servers.
    I can't see that it gets as far as the exchange server
    I would accept the argument re antispam score - however - these filters are disabled?
    Email is delivered instantly without email attachment.  Also emails with attachments are received instantly from all other exchange servers I have used to test.  Also using Trend.  I have tried from exchange 2003, 2007 and 2010 - all ok.
    LVL 14

    Expert Comment

    by:Shabarinath Ramadasan
    Check this link. If you dont see any trace where the mails are getting stuck, you can contact google asking for assistance.

    Occasionally, Gmail IP addresses are included on 'suspicious' lists by third-party organizations, like SORBS. Here are some suggestions that will help your domain2 receive valid messages and maintain a low level of spam:

        Try using a spam classifier, like SpamAssassin. When determining if a mail is valid, spam classifiers consider many aspects of the message, rather than just looking at the IP address.
        If you use a third-party block list, you should have a whitelisting mechanism in your SMTP3 gateway.
        Using only one list, such as SORBS, is not recommended.
        Avoid using lists that only expire entries after long periods of time, or even worse, never. We recommend using a 48-hour list that only keeps records of recent spam activity.

    If your domain still has trouble receiving messages from Gmail users, please follow the troubleshooting steps below. At each step, we'll provide instructions or further questions to help narrow down the issue you're facing.

    Accepted Solution

    this turned out to be an issue with Draytek Vigor Pro 5510 - there are several anti intrussion. anti spam,  Anti Virus featurespolicies that are active.  Althought these services were not enabled, the policies were active.  I have no idea why it suddenly became an issue, but had MS assist in troubleshooting exchange 2007 issues - and after lots of diagnosis - when these polices were disabled on the router - everything worked fine again.  It took some 48hrs of troubleshooting this.


    Author Closing Comment

    This is how I fixed it - this might benefit someone else.

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