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Exchange 2007 sp3 within SBS 2008: some outside recipients do not receive PDF's

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  • Exchange 2007 sp3 within SBS 2008: some outside recipients do not receive PDF's

    Hello.
    I had Exchange sp1 belonging to SBS 2008 and i updated to SP3 with no Rollup updates installed to see if I could solve the following problem:
    . Some recipients to which emails are sent with a PDF attachment receive the emails but with no attachment;
    . The senders are using either MS Outlook 2003 and Outlook 2007; the recipients are using Windows Live Mail or Outlook Express.
    . I'm using a smarthost routing the emails to the corporate site ( whose mail servers are hosted altogether with the site itself in a hosting company )

    I have tried:
    . Disablling all spam rules on EXchange
    . Setup MS Outlook to format HTML instead of using Word to compose new emails

    There are no errors and the emails have the attachments in the Sent folder.
    The problem continues. Did anyone have the same problem? What can be done?
    Thanks.

  • #2
    Re: Exchange 2007 sp3 within SBS 2008: some outside recipients do not receive PDF's

    I would argue that the fact that some outside users are not receiving attachments, while others are, suggests the issue is not with your infrastructure.

    Are you using an external service like mimecast at all? (you mentioned a smarthost)

    Are the external recipients using any spam filtering services at all"?

    Take a look at your message tracking logs, and the size of the email where it's reported as being stripped.
    then ask your smart host to look at the size of the email when they send it out their next gateway.
    If it's all still the correct size up to that point, it's not your issue.
    Please do show your appreciation to those who assist you by leaving Rep Point https://www.petri.com/forums/core/im.../icon_beer.gif

    Comment


    • #3
      Re: Exchange 2007 sp3 within SBS 2008: some outside recipients do not receive PDF's

      Hello, tehCamel.

      When I say SmartHost I mean for SMTP server of the site itself ( sorry if it is a wrong term ).
      I did a SetContentFilter exclusion tonight for the site using ECS to see if somehow Exchange is blocking the attachment.
      I think that there may be some kind of problems with the ouside users but... I have setup several Exchange 2003 and everything was strangley simpler than 2007 - 2007 seems to have lots of options, many of which are hidden on ECS.

      I will ask tomorrow for a new test. If this continues to be wrong, I will follow your advice in monitoring the size os the emails when it arrives and leaves the external SMTP Server of the site.

      Thanks.

      Comment


      • #4
        Re: Exchange 2007 sp3 within SBS 2008: some outside recipients do not receive PDF's

        There are known issues with attachments and Exchange 2007 SP3. These are resolved by rollup 4, I would suggest you update your server.

        ALWAYS, ALWAYS ensure that you are on the latest updates before seeking assistance because otherwise you will simply be told to update and then come back.

        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: Exchange 2007 sp3 within SBS 2008: some outside recipients do not receive PDF's

          Hello, Sembee.

          I haven't updated with the latest Rollup because I came across several people complaining about the latest one.

          But I will follow your suggestion and install the latest one, ie, Rollup nš 5 for Sp3.

          Thanks.

          Comment


          • #6
            Re: Exchange 2007 sp3 within SBS 2008: some outside recipients do not receive PDF's

            You will always find people who like to complain about anything from Microsoft, even though in many cases the cause is not Microsoft related.

            There have been some issues with rollups in the past, but the current roll up is fine. I have it deployed on all systems that I manage.

            If your SBS is setup correctly then the management console updates should prompting you to approve it. I work on the simple basis that when the update appears on Microsoft Update (and therefore WSUS) it is good to install, as Microsoft have delayed that deployment route in the past with troublesome updates.

            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

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