Outlook 365 for Mac - not sending attachments

Hi All,

we recently upgraded to the new version,

Sending mail attachments would remove when sending to emails.

Steps involved to try and fix that didn't work:

1. Uninstalling all Microsoft Outlook files and reinstalling. (didn't work)

• Uninstall Outlook by deleting to trash.
• Deleting the main profile in the folder:
• ~/Library/Group Containers/#######Office/Outlook/Outlook 15 Profiles
• Followed this link: Outlook Mac - Clear everything out and start again - Microsoft Community
• Then reinstalling outlook again. not working.

1. Removing Microsoft license. (didn't work)

• We also removed the licensee from office to see if that works via the license removal tool.
• How to remove Office license files on a Mac - Microsoft Support

None of these options worked.

What worked

The only fix for us was to downgrade just office. we selected V16.59 but maybe a slightly newer version will work until Microsoft fix these issues.

Follow the Uninstall all Microsoft Outlook files procedure. then install via the Update history for Office file supplied bellow.

Link here for anyone with the issues.

Update history for Office for Mac - Office release notes | Microsoft Learn

Hope this helps while Microsoft get their act together :)

PS. don't forget to turn off mac office auto updates.

We removed the HubSpot add-in from all devices and everyone is able to send attachments without issue.

Hi Benjamin, I updated Outlook 365 to the last version 16.76 and the problem seems gone. We also use HubSpot and I already asked our IT to open a support ticket to check the issue on their side.

I have 16.76 and the issue still persists.

Same as everyone -

Mine is PDF attachments disappear.

I can then reply all to the send message missing the attachment and re-attach and it then works.

I don't use Hubspot and I still have the attachment issue, so I don't think Hubspot is the root cause, sadly.