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Some attachments are corrupt when sent from Outlook for Mac - help! RRS feed

  • Question

  • I'm having a really strange issue that I can't figure out.

    I've tried sending a Word document and a PDF via Outlook for Mac and the recipients have the following issues:

    1. The Word document opens but it's blank

    2. The PDF has two different results, either a) They get the message "Adobe Acrobat Reader could not open 'xxx.pdf' because it is either not a supported file type or because the file has been damaged (for example, it was sent as an email attachment and wasn't correctly decoded), or b) it opens but there also appears to be a second identical document that won't open.

    I've then sent the exact same documents using my yahoo account and they can be opened no problem (the same if I save them in a Google Drive folder and send the recipient a link).

    However, this only happens with documents created on my Mac. If I send someone a pdf I received from a third party, they open fine.

    I'm guessing it has something to do with Word for Mac that is the original software I'm using to create or edit these files before saving some as PDFs and others as Word.

    I've searched online and can't find anyone else with the same issue. Any ideas?

    Saturday, December 8, 2018 10:25 AM

All replies

  • Hi Losttracks18,

    Does this issue happen to all recipients?

    If you send an Excel attachment, can you reproduce this issue?

    >> I've then sent the exact same documents using my yahoo account and they can be opened no problem

    Do you add your yahoo account to Outlook for Mac?

    Have you tried sending word or PDF attachment via the web mail with the same email account configured in Outlook for Mac? Will same error occur?

    To narrow down this issue, we can also configure another email account on this problematic client to see if same error occurs.

    Besides, please check sent item folder and then see if attachments can be opened normally on your side.

    What’s the detailed version of Outlook for Mac? Please install the newest updates to check the result.

    Any updates, please feel free to post back.

    Regards,

    Perry


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    Monday, December 10, 2018 3:12 AM
  • Hi Perry,

    Thanks for taking the time to respond, I appreciate it.

    To answer your questions:

    1.  Yes it happens to everyone, none of the recipients can open them, across Mac, PC or mobiles.
    2. I just tried sending an Excel and the same thing, I can't open it as a recipient in another email account (yahoo).
    3. Yahoo is separate, in my Mail account on the Mac
    4. If you mean, logging directly into Gmail (which is who the account is with) and sending it directly from Gmail (cutting out the middle step of the Outlook front-end) then no, the problem doesn't occur, the documents open fine.
    5.  I just added my yahoo account to Outlook and tried send a pdf to my wife and the same thing occured, she couldn't open it
    6. Checking the sent folder - the attachments can be opened normally
    7. Outlook version 16.4.4 (I tried updates but it says I'm up to date)

    Finally, I had one thought, the documents I'm attaching are all stored in my Google Drive. I moved one of the documents to the Mac folder and attached it and on receipt I could open it!

    So I've identified what the problem is, documents stored in Google Drive (Docs) won't open when sent via Outlook but will open when sent via another client (i.e. yahoo). What would cause this? Is there a lag in the upload time meaning documents aren't fully attached to the email in Outlook at the moment I'm sending them?


    • Edited by Losttracks18 Monday, December 10, 2018 10:03 AM bad grammar
    Monday, December 10, 2018 9:58 AM
  • Hi,

    Do you have any antivirus software running on your computers? If yes, please temporarily close these programs to check the results.

    Currently, I haven’t found official articles regarding this issue. We can also create a new profile on one problematic client to test the results.

    Regards,

    Perry


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    Wednesday, December 12, 2018 9:10 AM
  • Hi,

    As far as I'm aware I don't have any antivirus software running on my mac. Another issue also started today whereby I sent a client (and later a test address) a Meeting invite from the Outlook Calendar which they were unable to accept. Basically the email contains the info in the header but the body of the email is blank. I'm wondering whether to just get a Microsoft laptop to use for work purposes as I'm assuming Outlook would have less issues with that than the Mac.
    Thursday, December 13, 2018 5:35 PM
  • Hi,

    As this issue occurs to everyone, we can use a "clean startup" to determine whether background programs are interfering with Office for Mac. Please check the details in this link.

    In your case, you can uninstall Outlook for Mac completely and then reinstall to check the results.

    Reference: Troubleshoot Office for Mac issues by completely uninstalling before you reinstall

    Regards,

    Perry


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    • Proposed as answer by Perry-Pan Monday, December 17, 2018 5:48 AM
    Friday, December 14, 2018 5:51 AM