Unable to Attach Files Outlook for Mac

Hi Mike Rothenberg,

Thank you for reaching out. My name is Furkaan, a user just like you. I’d be happy to help you with your concerns. It's understandable that this recurring issue with attaching files in Outlook for Mac is frustrating. While restarting your Mac has worked as a temporary fix, let's try some other troubleshooting steps that might provide a more permanent solution:

Update macOS and Outlook:

Ensure you have the latest version of macOS installed. Go to System Preferences > Software Update and install any available updates. Update Outlook itself. Open Outlook, go to Help > Check for Updates and install any updates for Outlook.

Reset Outlook Preferences:

Quit Outlook. Open Finder and go to the "Go" menu. Select "Go to Folder." Type ~/Library/Group Containers/UBF8T346G9.com.microsoft.outlook in the path bar and press Enter. Delete the contents of this folder (but don't delete the folder itself). Restart Outlook. This will reset your Outlook preferences to default.

Check for Conflicting Add-ins:

Sometimes add-ins can interfere with Outlook's functionality. Start your Mac in safe mode. In safe mode, only essential applications load. If you can attach files in Outlook while in safe mode, then an add-in might be causing the issue. Restart your Mac normally and try disabling Outlook add-ins one by one to identify the culprit.

Consider Antivirus Interference:

Temporarily disable your antivirus software to see if it's blocking file attachments. Remember to re-enable it afterward as it's important for your Mac's security.

Contact Microsoft Support:

If none of these steps resolve the issue, consider contacting Microsoft's dedicated in-app support for Outlook for Mac. They can provide more targeted assistance based on your specific situation.

If you have any additional questions or concerns, please don’t hesitate to reach out. Give back to the Community. Help the next person who has this issue by indicating if this reply solved your problem. Click Yes or No below. Best Regards, Furkaan

Has anyone found a resolution to this issue? I have this same issue and it's becoming extremely annoying.

The only solution when this randomly occurs is to completely restart my computer. I have yet to know when it happens and how to prevent it.

Same here and it's becoming extremely frustrating as I have multiple files/apps open, have to close them and reopen once computer is rebooted. Not ideal. I usually save a draft of the e-mail, open outlook web and attach the file from there. It works but is annoying.

The same goes for me. To fix this, I switched to the legacy version (in the menu bar, click Outlook > Legacy Outlook). It's annoying since I've gotten used to the newer version, but it seemed to be a quick fix while Microsoft identifies this as a widespread problem and works on a solution.