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

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  1. Anonymous
    2023-09-22T08:29:15+00:00

    I've given up on direct updates from Microsoft, and now use this as the best source of information (credit to the other person who posted this earlier in the thread): https://support.nhs.net/2023/07/microsoft-365-alert-service-degradation-exchange-online-users-email-with-attachments-sent-from-outlook-for-mac-and-the-outlook-mobile-app-may-be-delivered-without-attachments/

    Latest updated from yesterday 21st September: Microsoft deployed a fix to update attachment logic that they have confirmed will reduce instances of this issue from occurring when users frequently add and remove attachments by 40 percent. Their development of a long-term solution to this problem is contingent on the telemetry they are collecting subsequent to the delivery of their attachment logic update, and Microsoft will provide a better estimation on the development of the long-term fix when available.

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  2. Anonymous
    2023-09-18T15:14:37+00:00

    16.78 still hasn't rolled out for me and I have Beta chosen. Mine seem to be behind most. Not sure why, but still waiting. I've even tried to force an update by deleting the app and reinstalling, still no update. URG.

    We need an update from Microsoft! It's been almost a month now since their last update.

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  3. Anonymous
    2023-09-01T14:06:29+00:00

    It has been but the more people that report it, the more they see the issue. Go to your Help tab and click contact support. You can report the issue there. Everyone should do this. The squeaky wheel gets the oil.

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  4. Anonymous
    2023-09-01T07:24:40+00:00

    I'm not sure which step here works, or if it's a combination of all of the above, but following these three steps always seems to resolve the issue for my team (all three steps are from previous suggestions in this thread):

    In Finder:

    • Press CMD+Shift+G
    • Go to the following directory: ~/Library/Group Containers/UBF8T346G9.Office/Outlook/Outlook 15 Profiles
    • Right-click (or alt-click) on the 'Main Profile' directory
    • Choose "Get info"
    • In the section at the bottom, click the padlock icon and grant permissions
    • Next to 'Everyone', choose 'Read & Write'
    • Click the drop-down button with the round circle containing 3 dots, then choose 'Apply to enclosed items...'
    • Click the padlock again to save the change, then close all the Finder windows

    In AutoUpdater:

    • Click the 'Advanced...' button in the bottom right corner
    • Switch to the Beta Channel
    • Wait for it to refresh, then AutoUpdater should have a new update
    • Install the updates for AutoUpdater until you're fully up to date
    • It should then display updates for all of your Office apps
    • Download and install the latest version of Outlook (16.78 at the time of writing)

    In Outlook:

    • Click Outlook (in the top-most menu, next to the Apple icon)
    • Choose 'Settings...'
    • Choose 'Privacy' (third icon in bottom row)
    • Un-check the checkbox 'Turn on optional connected experiences'
    • Close the window
    • Quit Outlook
    • Open Outlook, and click the button to accept if a prompt pops up
    • Go back to Settings... > Privacy > Re-check the box you previously un-checked
    • Close the window
    • Quit Outlook
    • Open Outlook

    As previously mentioned, this combination seems to permanently fix the issue for anyone here in my team that encounters it. Hopefully this will help others out there who are pulling their hair out over this ridiculous bug!

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  5. Anonymous
    2023-09-01T06:13:43+00:00

    Is there a way to escalate this as a problem to support or similar?

    It is causing me A LOT of problems with clients, it is negatively impacting my business.

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