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
    2023-09-01T07:24:40+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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  2. Anonymous
    2023-08-18T20:21:09+00:00

    I must say that my issues began with installing the Hubspot plugin and stopped after reverting to the old one, removing the Hubspot plugin and updating to the new version again. Now it is working again for 3 weeks, flawless.

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  3. Anonymous
    2023-08-16T08:45:09+00:00

    Just did this - removed Hubspot add-in and sent a couple of test emails. All good so far... :)

    J

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  4. Anonymous
    2022-08-12T06:11:21+00:00

    Just started to have problem too

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  5. Anonymous
    2022-05-27T18:18:45+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

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