Outlook unable to open/view/save PDF attachments from Mac Mail


  • Since the last patch, I have been having a problem with all my outook (2007 and 2010) users, where we cannot open/view/save PDF attachments send from Mac users using Mac Mail.  In the outlook message pane, it correctly shows the paperclip icon to indicate there are attachments, but in the preview pane, or when you open the message in its own window, no attachments show up. If you try and select "save attachments", the window opens, but no attachments are listed. 

    Users ARE able to view/save attachments using OWA and Blackberries (via BES) - the problem is only with the Windows Outlook client. 

    This problem is not specific to one particular mac users - it has come up from several different Mac Users (all using Mac Mail), from totally different companies/email servers/etc.



    Thursday, March 31, 2011 5:05 PM


All replies

  • Hello Tim,


    Last Patch? Did you installed Feb 2011 Cumulative update for Outlook 2007 and 2010? If not lets install these below updates for 2007 and 2010.

    Outlook 2010:;en-US;2475891       
    Word 2010:;en-US;2475888


    Outlook 2007: Description of the Office Outlook 2007 hotfix package (Outlook-x-none.msp): February 22, 2011


    What is the version of Exchange Server in your environment?

    Do you see the attachment in OWA or is it still hidden. However, the inline attachment is available for download in OWA?

    Please check if this KB article is applicable to your issue


    Are these HTML email + PDF attachments which are sent from MAC? These could be and HTML in the email is malformed due to which you cannot see the attachment in Outlook. If that is the case there is nothing much we can do.

    Check if Entourage compose preferences mail format set to HTML? If yes, change Entourage compose preferences mail format to default setting “Plain Text” and send out an email with PDF attachment and test the behavior.


    If above suggestion doesn’t help than I would suggest you open a support ticket with Microsoft as this would require in-depth troubleshooting to determine what is happening.


    Best Regards,

    Rashid Aga [MSFT]

    Sunday, April 03, 2011 9:48 AM
  • Your problem is that Outlook is seeing the Mac Mail message as HTML which appears to embed your attachments, but all you have to do is change your outlook message view to plain text to see them as attachment. After doing that it will work, I did hear from some of my users that they had to change global view to plain text for it to work. I'm a systems Manager who is an Apple Systems and network specialist, we are 80% mac and 20% Windows. I run into this every now and again.


    Hope this helps.


    Wednesday, May 25, 2011 7:11 PM
  • Hello,


    we have the same Problem with HTML-Mails with PDF attachments, sended from Apple. Outlook 2003/2007 shows correctly the paperclip icon, but in the message is no attachment. In OWA we can save them and open. Alle solutions from Rashid Aga have not helped us.


    Do you found a working solutions?



    • Proposed as answer by LordMcRoy Tuesday, July 05, 2011 1:25 PM
    • Unproposed as answer by LordMcRoy Tuesday, July 05, 2011 1:25 PM
    Monday, June 20, 2011 9:55 PM
  • we have exactly the same Problem with HTML-Mails with PDF attachments, sended from Apple (as WoWn describes it). 

    All solutions above have not solved our problem.

    Please help

    Tuesday, July 05, 2011 1:53 PM
  • This problem originally cropped up back in March/April, and then seemed to resolve itself after a couple weeks, but then I have had a few problems again in the last week or two.  We have a hosted Exchange Server (Elephant Outlook), so I can't speak to what version and patches they have, but our client machines are certainly fully patched.

    In terms of a solution when it does happen, several things have worked:

     - Use Outlook Web Access (OWA) to view/save attachments, rather than outlook desktop client.

     - Ask original sender to "attach", rather than "embed" the files

     - Forward the email with the missing attachements to yourself, but forcing message type to PLAIN TEXT (instead of HTML).


    All of these usually solve the problem for us.  It is certainly a huge pain.  We are in the broadcast and entertainment industry, and many of our clients and suppliers are on Mac.



    Tuesday, July 05, 2011 5:16 PM
  • Thanks Tim

    But the Workaround "- Forward the email with the missing attachements to yourself, but forcing message type to PLAIN TEXT (instead of HTML)."  does not work. If I do that, there is no paperclip and no attachment visible in the sent and inbox Item. Not even if I set my outlook in the "view and send all Emails in plain-text" mode.

    OWA works fine, but this is not a solution, it's a workaround :)


    Now, we have fixed this issue (Mac-Mails with attachments) with this KB article: after that and restarting the Transport-Service on our EXC2007 Server all attachments are visible and accessable from the new incomming MAC-Emails. Special thanks to Rashid. :)


    • Edited by LordMcRoy Wednesday, July 06, 2011 2:14 PM Issue fixed
    Wednesday, July 06, 2011 12:42 PM
  • Roy,


    I am not sure why the plain text work-around doesn't work in all cases, I just know that it has worked for me.  Really all of the things I have done are work-arounds, and not solutions.  It would be nice of Microsoft could fix this properly at their end.


    Good luck!

    Wednesday, July 06, 2011 4:32 PM
  • We are having the Same problem. 
    Wednesday, March 13, 2013 10:13 AM
  • Do you know if this will be fixed in Outlook 2010?  I often use Yahoo's web mail server to read and write e-mail, move sent e-mail from my Yahoo sent box to Yahoo inbox, and later download it all into Outlook 2010.  When I send a PDF attachment to someone and later download my own e-mail, Outlook 2010 shows the clippy icon saying that there's an attachment, but Outlook 2010 doesn't display the attachment itself.  Outlook 2010 sometimes works and sometimes doesn't work.  I doubt very much that the server side matters at all (Exchange or Yahoo or anyone else).  I looked at Yahoo web mail again and the attachment is really there.
    Sunday, March 29, 2015 1:51 AM