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  • smtp Mail disappearing in exchange

    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 electric.net 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,

  • #2
    Re: smtp Mail disappearing in exchange

    If the message isn't in message tracking logs then it didn't reach Exchange.
    Primary cause for that is something blocked the message flow after it left the client and before it hit Exchange transport. AV, Antispam, firewall, something like that.

    I wouldn't flatten the existing Exchange server, as due to the tight integration with AD you would have to DR install it and then recover content etc.
    If the facilities are there to migrate to another server and/or version then that is what I would do. I would also be looking at anything third party on the server that could be blocking the traffic.

    Simon.
    --
    Simon Butler
    Exchange MVP

    Blog: http://blog.sembee.co.uk/
    More Exchange Content: http://exchange.sembee.info/
    Exchange Resources List: http://exbpa.com/
    In the UK? Hire me: http://www.sembee.co.uk/

    Sembee is a registered trademark, used here with permission.

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    • #3
      Re: smtp Mail disappearing in exchange

      Thanks Sembee,

      the only other thing that in on that Exchange VM is Exclaimer Mail Utilities (email signature software, which has to be installed on the exchange server to work).
      We do have journaling enabled as it's required for our DMS software. This adds an overhead to the exchange, but there's no real evidence that it's causing issues.

      I wasn't aware that there was anything else between the clients outlook install and the exchange server. We have sophos sbe installed across the domain and GPO turns off all domains, choosing to use the firewall on our draytek router instead.

      There seems to be quite a few other issues with the exchange install in general, ie
      1. iphones don't sync correctly periodically
      2. SSL certificates sometimes go boobs up
      3. at least one mailbox on a pc (cached exchanged mode) isn't replicated exactly when the same user logs into our RDS
      4. Had hiccups when trying to install service packs and/or rollups

      Comment


      • #4
        Re: smtp Mail disappearing in exchange

        The problems you have identified are not something I would be expecting to happen with a correctly functioning server.
        If possible I would be planning to replace the server with a fresh build of Windows/Exchange and do a swing migration.
        New/latest builds of all third party products, no upgrades from older versions first.

        Simon.
        --
        Simon Butler
        Exchange MVP

        Blog: http://blog.sembee.co.uk/
        More Exchange Content: http://exchange.sembee.info/
        Exchange Resources List: http://exbpa.com/
        In the UK? Hire me: http://www.sembee.co.uk/

        Sembee is a registered trademark, used here with permission.

        Comment


        • #5
          Re: smtp Mail disappearing in exchange

          Hi, thanks again for your reply Sembee.
          I built a new Exchange 2007 sp3 latest ru.

          Now, moving mailboxes from one exchange vm to another on the same host (but using different nics) is extremely slow when using the move mailbox wizard.
          The max mailbox size is 8gb. I set 60 to move on sunday and i'd assigned 25gb of ram to each mailserver. No other guests servers were on so no one was on the network.
          Yet, 24 hours only 18 of the 60 had been moved and most of them are less than 3gb in size.
          Does this sound about right or does it seem unusually slow?

          Would using the powershell console command to move mailboxes be any better/quicker?

          Thanks again.

          Comment


          • #6
            Re: smtp Mail disappearing in exchange

            Not really -- the EMC is a front end to Powershell anyway

            Not sure about the speed but it does seem slow

            btw, why aren't you using Exchange 2010?
            Tom Jones
            MCT, MCSE (2000:Security & 2003), MCSA:Security & Messaging, MCDBA, MCDST, MCITP(EA, EMA, SA, EDA, ES, CS), MCTS, MCP, Sec+
            PhD, MSc, FIAP, MIITT
            IT Trainer / Consultant
            Ossian Ltd
            Scotland

            ** Remember to give credit where credit is due and leave reputation points where appropriate **

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            • #7
              Re: smtp Mail disappearing in exchange

              If you are using the same host then you are moving the data around on the same storage system. That will be slow because Exchange is very storage heavy.

              Simon.
              --
              Simon Butler
              Exchange MVP

              Blog: http://blog.sembee.co.uk/
              More Exchange Content: http://exchange.sembee.info/
              Exchange Resources List: http://exbpa.com/
              In the UK? Hire me: http://www.sembee.co.uk/

              Sembee is a registered trademark, used here with permission.

              Comment


              • #8
                Re: smtp Mail disappearing in exchange

                The next logical step was to create a new 2k7 exchange box, as this doesn't cost us anything because we already have the licensing in place.
                Microsoft Tier 2 support don't know the reason we are having the problems described in the OP, and as such it could be at the exchange server OR client end.
                If we spent money on exchage 2010 plus all the CALS, to find the problem was still with us (and possiby client side), would cause.....err.....a lot of trouble to say the least.

                Comment


                • #9
                  Re: smtp Mail disappearing in exchange

                  Originally posted by Sembee View Post
                  If you are using the same host then you are moving the data around on the same storage system. That will be slow because Exchange is very storage heavy.

                  Simon.
                  I would have thought moving data on the same array is quicker than moving it across the network?

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                  • #10
                    Re: smtp Mail disappearing in exchange

                    Originally posted by k.jacko View Post
                    I would have thought moving data on the same array is quicker than moving it across the network?
                    No. If you are on the same array that is actually slower because you are reading and writing at the same time. The storage is thrashing against itself.

                    Simon.
                    --
                    Simon Butler
                    Exchange MVP

                    Blog: http://blog.sembee.co.uk/
                    More Exchange Content: http://exchange.sembee.info/
                    Exchange Resources List: http://exbpa.com/
                    In the UK? Hire me: http://www.sembee.co.uk/

                    Sembee is a registered trademark, used here with permission.

                    Comment


                    • #11
                      Re: smtp Mail disappearing in exchange

                      Hmmm...yeah make sense i guess.....bugger!!
                      Oh well, can't do much about that now.

                      Thanks

                      Comment

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