Outlook 365 for Mac - not sending attachments

Anonymous
2022-05-27T14:24:12+00:00

I have an issue whereby Outlook for Mac is losing attachments when sending emails (typically, but not exclusively, PDF files).

If a file(s) is/are dragged and dropped into an email it is shown as attached and appears to send as normal. There are no error messages or bouncebacks, and the first we know that the email has lost the attachment is when we are advised by the recipient. Then when checking the sent folder, the email is there but again without the attachments.

Doesn't do this every-time though... sometimes the email goes with the attachments as it normally should.

I'm using version 16.62 (22052500)

Has anybody else had this issue and is there a fix? Or is it a software glitch?

Outlook | MacOS | Legacy Outlook for Mac | For home

Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.

0 comments

240 answers

Sort by: Most helpful
Most helpful Newest Oldest
  1. Anonymous
    2023-07-06T17:02:12+00:00

    Hi,

    Take look here https://macadmins.software and download Outlook Update version 16.73.2. Before running the downloaded installer package, quite Outlook and move the existing Microsoft Outlook.app out of the Application folder. Otherwise the installer will run fine but probably won't downgrade Outlook.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  2. Anonymous
    2023-06-29T23:50:09+00:00

    I'm having the same issue with the same version 16.74.2.

    Steve Cox1's advice does work as a temporary fix but there really needs to be an update from MS as the reduced security of the fix isn't acceptable.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  3. Anonymous
    2023-06-13T15:32:15+00:00

    Same issue. I use MS365 for work and it’s embarrassing to send emails regarding an attached document and have it go missing in transit when corresponding with an executive.

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  4. Anonymous
    2023-05-26T15:14:31+00:00

    This is happening to me as well. I can not figure out what to do!!

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments
  5. Anonymous
    2023-05-24T17:20:45+00:00

    Hi Nathan

    Thank you for posting in Microsoft Community.

    I understand you have an issue with sending attachments in Outlook for Mac. Based on your description I noticed you're using the Beta version of Outlook for Mac please try to check if there is any update available, if yes please update your Outlook for mac.

    In the meantime please try the following suggestions:

    1. Please send a test mail with an attachment when your Mac is in safe mode ;
    2. On your Mac, choose Apple menu > Shut Down.After your Mac shuts down, wait 10 seconds.
    3. Press and hold the power button on your Mac until the startup options window appears showing available startup disks and...
    4. Select a startup disk.
    5. Press and hold the Shift key, click Continue in Safe Mode, then release the Shift key.
    6. If you have any anti virus, please try to disable it briefly then send the mail with an attachment to see if the issue persists.

    If the issue persists even after trying the suggestions above, I would suggest visiting our Outlook for Mac dedicated team by navigating to help> Contact support.

    Your understanding and Cooperation are highly appreciated.

    Sincerely,

    Momo Kamboni | Microsoft Community Moderator

    It's been nearly a year since this thread was created, and the issue still persists. When can we expect Microsoft to take responsibility and resolve the problem?

    Was this answer helpful?

    1 person found this answer helpful.
    0 comments