smtp Mail disappearing in exchange

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    Hi all,

    we’re desperate for help, and not even Microsoft themselves have come up with an answer for this.

    Over the past 4 months we’ve experienced, ‘seemingly’ randomly an amount of sent emails that do not reach their destination and simply disappear in our exchange 2007 SP3 latest RU.
    I supply details to our IT company of the exact time, date etc of the message, they search for it in the tracking filters, but cannot find it.
    The mail is sitting in the users sent items, evidence at least that it has gone through the process of being ‘sent’ to our smtp server so to speak.
    It may be that the user sends another email to the same recipient 10 mins later and it will be received. That’s the randomness for ya. :???:

    So, i asked our users to apply Delivery Receipts to every external email. If they receive a DR then surely that means its at least left our exchange server, and may possibly be caught up in the spam filters or further on that than.
    If they don’t receive a DR within 10 mins then i report it to our IT company, they search our exchange and as expected they cannot find the message.

    Our IT company had to elevate this to Microsoft as they couldn’t figure it out. MS had our IT company pipeline certain users and send their reports back to them.
    So far, 3 weeks later nothing tangible has come of this.

    As a company we are losing money and confidence (from clients) in our mailing system.
    I can’t find anyone else on the internet who is suffering from the same issues as us.

    Our users either work off their local pc (win7 pro x64) or via RDS (ws2008 r2), and there is no obvious pattern as to who falls foul to this issue and why. We all use outlook 2010 (x86)

    The only thing some users have said is that if they try to ‘resend’ or ‘forward’ an email that is sitting in their sent items and had otherwise got ‘lost’ and never reached its destination, it would still fail. However, creating a new message, and pasting the contents into it would often work fine.

    MS know about this, but again, no real answers as to why it happens.

    Our Exchange install is a hyper-v guest, so i’m wondering whether we should:
    a) flatten it and rebuild
    b) make a new vm with Exchange 2010 (or later) and migrate
    c) go to hosted exchange for approx. 70 users

    Your thoughts would be greatly appreciated as we’re realy struggling with this.

    Many thanks in advance,

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