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Certain recipients unable to open attachments - winmail.dat RRS feed

  • Question

  • Exchange 2007 SP2

    Outlook 2007 SP2 (no 2003, no 2010, yet)

    OWA - in IE7 and IE8

    Recipient email system: various, those above and webmail with Google, Yahoo, MS, AOL....

    -----------------------------------------------

    OK,

    A number of email recipients our users correspond with are unable to open attachments - or simply do not receive them (the attachment, not the message itself).

    I thought it had to do with Outlook and instructed users to send in Plain Text format for the "problem recipients", or configure, in Contact properties, "Use MAPI rich text format - NEVER".

    But recently, someone who uses OWA only (no Outlook) informed me that her recipient did not receive an attachment.

    I am still looking into this (you have to take user incompetence in account, and inaccurate descriptions of the issue) but still, I have to ask with them:

    "Why can't this just work?"

    Other question:

    If I run a PowerShell script that would set the MAPI setting mentioned above to NEVER for everyone, does that mean, in essence, that all communciations would be in Plain Text format and we would loose any bold, italic, underline, and bullet formatting?


    Thursday, May 19, 2011 2:03 PM

Answers

  • It's all or nothing.  Forcing plain text should fix the Winmail.dat attachment, but you lose the rich text.  That's all the Winmail.dat file is, the rich text formatting data.


    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Wednesday, May 25, 2011 5:30 PM

All replies

  • What happens when they try?  Always post exactly what you experience.

    OWA and Outlook block certain attachment types, and that is something that is configurable.  You can Google "Outlook attachment block" and/or "OWA attachment block" for more information on that.


    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Thursday, May 19, 2011 3:17 PM
  • Need more info. It could be many reasons, it could be blocked on their end, it could be a malformed mime attachment email that won't render correctly etc. Need to do some more troubleshooting.

    1. Is the target recpient not able to receive any attachment type?

    2. Does the recipient not see the attachment? Are they getting something else like ATTxxxx, winmail.dat, missing paper clip etc?

     

     


    James Chong MCITP | EA | EMA; MCSE | M+, S+ Security+, Project+, ITIL msexchangetips.blogspot.com
    Thursday, May 19, 2011 5:47 PM
  • Right, more information.

    On our end at least, I have not blocked any attachment types (extensions, right?) other than what is blocked by default.

    Attachments are always Word documents (.doc, .docx), Excel and PowerPoint.

    Lastest example was a .pptx PowerPoint document.

    Nothing like .exe or .bat (nobody here would be sending files like that).

    -------------------------------------------------------------------

    In the past, recipients have seen winmail.dat, or simply nothing.

    The changed MAPI setting resolved this so far.

    This is the first time I've heard this this happening with OWA.

    Once again, this was a .pptx document (PowerPoint).

    I'm trying to get more information from the person who has had this problem most recently.

    Thursday, May 19, 2011 8:23 PM
  • Do you have a firewall doing SMTP "fixup" or other "helpful" tasks, antivirus or antispam appliance or service, or an SMTP relay server between the Internet and your Exchange server?  Those things can screw up message formats.
    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Thursday, May 19, 2011 10:06 PM
  • Nothing like that for outbound mail (inbound is filtered by Postini). All antivirus is on the server itself. Fact of the matter is that to our knowledge most of the recipients DO get mail sent to them. No response yet to my request for additional info in this last case.
    Friday, May 20, 2011 12:15 AM
  • How do your users enter the e-mail addresses of the recipients?  Do they have a contact or is there a contact in AD?  Make sure that the recipient object isn't configured to force plain text mail.


    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Sunday, May 22, 2011 4:58 AM
  • 1. There is a contact in AD - do you mean the GAL? 2. I have configured the MAPI setting as mentioned above: "Use MAPI rich text format" - NEVER. This has allowed - affected - users to get attachments correctly instead of the dreaded winmail.dat file in place of the attachment.
    Sunday, May 22, 2011 9:19 PM
  • Hi Le Pivert,

    Did you check below:
    1.In the Exchange Management Console open "Organization Configuration" -> "Hub Transport"
    2.Click the tab "Remote Domains"
    3.Open "Default" and goto the tab "Format of the original message sent as attachment to journal report:"
    4.Under "Exchange richt-text format:" change the setting to "Never use" and click OK
    And did you make some tests that sending the email in the plain text?
    Which version of outlook do you use to send email, I would update them for the latest version, and and make some test.
    Per your description, the recipients all could receive the attachement except for the webmail Google, Yahoo, MS, AOL, right?

    Regards!
    Gavin

    Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.
    Tuesday, May 24, 2011 9:27 AM
  • Hello Gavin,

    No, I have not configured anything under the Remote Domain tab.

    As far as Plain Text goes, do I want to use Plain Text or not?

    I think it would be a more compatible format than the rich text format.

    Setting the "Use MAPI rich text format - NEVER" setting seemed to be an improvement for many users.

    But... users would lose the ability to format the messages with bold, underline, italics and bullets.

    Right?

    And in one of the posts above (last one from Ed Crowley), it almost sounds as if I am NOT supposed to force use of a non-MAPI format (???).

    Even though this has worked for them.

    Otherwise, the recipients do not use Outlook at all - only webmail.

     Most of all, I have to get back to the person that was complaining about this because they want a solution but do not respond to my followup questions.

    Wednesday, May 25, 2011 2:22 PM
  • It appears you are using that setting the way it is designed.  You want to send plain text messages to users with clients that can't handle rich text.

    Senders can still compose messages with bullets, italics, underline and bold, but that will be stripped out in transport.  You want rich text, right?

     


    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Wednesday, May 25, 2011 3:30 PM
  • I want, in order of importance:

    1. A format that allows the recipient to see and be able to open any attachments (rather than see nothing or the dreaded winmail.dat file).

    EDIT -----> If that MUST be Plain Text, then I (and my users) can live with that.

    2. Preferably, retain the ability to format the body of the email message.

    This has come up in another discussion:


    http://social.technet.microsoft.com/Forums/en-US/exchangesvradmin/thread/e43d4cf3-cfcd-4978-87ef-c509fc2febe8

     

    Also, would HTML format not achieve both of those objectives? 


    Wednesday, May 25, 2011 5:18 PM
  • It's all or nothing.  Forcing plain text should fix the Winmail.dat attachment, but you lose the rich text.  That's all the Winmail.dat file is, the rich text formatting data.


    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Wednesday, May 25, 2011 5:30 PM
  • I have observed that PPT 2007 documents mailed from a particular user always result in mail.dat attachements. Outlook 2007, internet email. I checked all the settings and they are the same as mine and I have no problems. So I watched how the user sent the message. Two methods by the same user result in different results.

    1. Start a new email, attach PPT document, send. Works perfectly. PPT doc receieved.

    2. Open doc in PPT, Select Office Button: Send: Email. Checked email settings, all are the same (HTML) but the resulting email had winmail.dat instead of PPT attachment.

    The problem must be in how PPT 2007 is communicating with Outlook 2007 for this function


    As a workaround, I have instructed the user not to use the send from an open PPT method.

    Installing this fix cured the problem:

    http://support.microsoft.com/kb/958012

    • Proposed as answer by rahughes Thursday, June 23, 2011 2:15 PM
    Thursday, June 23, 2011 1:24 PM
  • Yeah, it looks like PowerPoint is creating a new message of type Rich Text, which means Winmail.dat to clients or e-mail systems that can't handle the rich text.
    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."
    Thursday, June 23, 2011 8:51 PM