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Outlook email attachments suddenly not uploading to OneDrive

JLCOEH 0 Reputation points
2025-12-04T05:56:20.0166667+00:00

I have a Hotmail personal email account from the late 1990s that I now sign into via Outlook.

MacBook Air/MacOS Monterey operating system

I used to be able to click attachments in my personal email account and save them with easily to OneDrive on the web.

Now (Dec 2025) when I try to do this, every attachment shows a message with an X saying "This file could not be uploaded to OneDrive."

No error message from Outlook/OneDrive explaining why email attachments are not uploading to the cloud anymore.

I have 1.1 GB of space remaining in my 5 GB account and the files I'm trying to upload are all low double-digit MB files; there should be no storage space issue.

I encountered this problem right after organizing my OneDrive files and had deleted the Email Attachments folder in OneDrive (all of the files that were in it I moved into specifically-named folders).

Is this the problem?

If so, I created another Email Attachments folder in OneDrive but to no avail. Email attachments in Outlook will still not upload to OneDrive.

Outlook | MacOS | Legacy Outlook for Mac | For home
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  1. Q&A Assist
    2025-12-04T05:57:40.8566667+00:00
    AI generated content. This question contains an answer created with AI from Q&A Assist. Learn more

    It seems you are experiencing issues with uploading email attachments to OneDrive from Outlook on your MacBook Air. Given that you have already deleted the Email Attachments folder and created a new one without success, it's possible that the issue may be related to the way Outlook interacts with OneDrive or the specific settings on your account.

    Here are a few troubleshooting steps you can try:

    1. Check OneDrive Status: Ensure that OneDrive is running properly on your Mac and that you are signed in with the correct account.
    2. Storage Limit: Although you mentioned having 1.1 GB of space left, verify that there are no restrictions on the types of files you can upload or any other account limitations.
    3. Update Outlook: Make sure that your Outlook application is updated to the latest version, as older versions may have bugs that affect functionality.
    4. Reboot and Retry: Sometimes, simply restarting your Mac can resolve temporary issues with applications.
    5. Test with Different Files: Try uploading different types of files to see if the issue is specific to certain file types or sizes.
    6. Contact Support: If the problem persists, consider reaching out to Microsoft support for further assistance, as they may have additional insights or solutions specific to your account setup.

    If the issue started after organizing your OneDrive files, it may be worth checking if there are any sync issues with OneDrive itself. You can also try accessing OneDrive directly through a web browser to see if you can upload files manually, which could help isolate the problem.

    References:

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