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Attachments sent from Mail do not show up in Outlook

62392 Views 91 Replies Latest reply: Dec 30, 2013 10:52 AM by Jhornby RSS
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bdietz72 Level 1 Level 1 (0 points)
Currently Being Moderated
Jul 7, 2011 8:32 AM

Have been running into a problem wherein attachments sent from Apple Mail do not show up for Outlook users they are sent to.  If I switch and send the same attachment via GMail for instance it shows up fine.  Apple Mail locally shows the attachment as having been sent.  Anyone seen this before or have any thoughts on how it might be fixed? 

  • Klaus1 Level 8 Level 8 (43,300 points)

    Do you send them as Windows friendly attachments?

    20" 2.1GHz iSight iMac G5,, Mac OS X (10.5.8), iLife 9 but iMovie 6, QTPro 7.6.9, Safari 5.0.5
  • Klaus1 Level 8 Level 8 (43,300 points)

    It must be a setting in Outlook that needs tweaking.


    If they show as sent, then they were sent.

  • Jeremy Kinsey Level 1 Level 1 (5 points)
    Currently Being Moderated
    Jul 26, 2011 1:44 PM (in response to Klaus1)

    It's not an Outlook problem. Its an apple mail problem. The problem occurs with all mailers except apple mail.

    When will there be a fix?

  • Aprilstern Level 1 Level 1 (0 points)

    I've also been having this problem.  Receivers say they don't get the attachments despite them being sent as windows friendly.  They show up as sent in my outbox.  Any suggestions?

  • Aprilstern Level 1 Level 1 (0 points)

    Should also note that the problem occurs with jpeg files as well. 

  • Jeremy Kinsey Level 1 Level 1 (5 points)

    Wonder why Apple is so hush hush about this bug?


    When will there be a fix???

  • billr99 Level 1 Level 1 (0 points)

    Same problem. Have tried both suggestions I was able to find with no joy.  That is, change from Rich Text to Plain Text and to do this mod "defaults write DisableInlineAttachmentViewing -bool yes". And in both cases, attachments, JPGs in this case, were sent as "Windows friendly".  A major screw-up by Apple it would seem.

  • davidpetree Level 1 Level 1 (10 points)
    Currently Being Moderated
    Aug 23, 2011 7:39 AM (in response to billr99)

    Hey guys


    I have a quesitons as i have not seen this behavior and it all works fine for me. So, i want to throw some questions out to you guys who its failing on.


    1. What OSX version are you running? I Have tested with 10.7.1 and 10.7.2 and it works

    2. Is this only failing internal or external from your exchange? I have tested interneal and external and it works

    3.  What do you have your attachment settings at? I have mine set to "alwasy inset at end of message" and have tested "Windows frendly" both worked fine.


    So, basiclly, i cannot get this to fail as you guys have described but i beleive you have a problem, i just wanted to help narrow down the issue.

  • Jeremy Kinsey Level 1 Level 1 (5 points)

    David, it does fail. The problem is you are likely emailing other Mac users. If that is not the case, please let us know exactly what kind of users you are emailing attachments to, what OS and email client they are using. 


    Keep in mind, this only affects IMAGES, not PDF's or other attachments like zipped files.


    Also good to note is that many of the more advanced users can figure out how to right click to open/view the attachment.  


    However, MOST of the windoze world is not that "advanced"... My guess is you are not sending to a wider audience of windoze drones like many of us are forced to do.



  • davidpetree Level 1 Level 1 (10 points)



    Thank you for your response.


    I do not disagree its failing for people, I'm just trying to narrow it down.

    I emailed Mac and windows users.


    But I emailed a document. Thank you for telling me its images only. I will start testing that when I get back from lunch. Now you have giving me some more to work with I can do some more testing.


    Thanks again

  • h-q Level 1 Level 1 (0 points)
    Currently Being Moderated
    Aug 24, 2011 12:37 AM (in response to bdietz72)

    I have the same problem where certain attachements sent from Apple Mail do not appear in Outlook.

    • The problem appears on both OS X 10.7 and 10.7.1. I'm using Apple Mail with Exchange 2007.
    • I have checked that the attachement does apper in my "Sent" items on Apple Mail, but not in the same folder on my Outlook 2007 (Windows).
    • The problem is with PDF files as well.
    • I do have both "Always Send Windows-Friendly Attachements" and "Always Insert Attachements at End of Message" checked. (Doesn't make a difference).
    • The problem only occurs when replying to (especially) long email messages. If I compose a new message, this never happens.
    • My recepients use Outlook 2007 + Exchange 2007 (I'm using the same Exachnge with Apple Mail), BlackBerry and Entourage 2008 + Exchange 2003.


    This has been a major source of embarrasement.


    In my personal view, Apple Mail lags behind for the Enterprise. It has numerous nifty features that can increase productivity dramaticaly, yet it's missing some essentials. It doesn't even support Push Mail for Outlook 2007 (but my iPhone does!)

  • Jeremy Kinsey Level 1 Level 1 (5 points)
    Currently Being Moderated
    Aug 24, 2011 7:42 AM (in response to h-q)

    You hit the nail on the head. It is a HUGE EMBARRASEMENT.


    Apple we need a fix ASAP. 

  • AOrlandini Calculating status...

    Still no solution to this annoyng and frustrating issue. I have to keep using gmail web interface and this is tedious when having to send several pictures to PC users, after we look like the ones not able to send attachments!

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