Creating calendar events and attaching files from OneDrive

Question

My other coworkers can make a calendar event and attach a file to it rather than the link in the body of the calendar invitation. Every time I try to attach it to the email it loads about 80-90% then stops loading, I've stepped away for 10 minutes or so to give it time and it still does not work. How do I fix this?

Answer 1

Dear @Kassondra Davis,
I understand that you are creating calendar events in Outlook on the web. When you try to attach a file from OneDrive, the upload almost finishes but then stops. Other coworkers are able to attach files, but it does not work for you.

To help us narrow this down, could you please confirm:

Which browser are you using (Edge, Chrome, Firefox, or another)?

Does the issue happen with all files, or only specific files?

Is the file already fully saved and synced in OneDrive before attaching?

Does the issue still occur if you try using a different browser or an InPrivate/Incognito window?

Approximately how large is the file you are trying to attach?

Does attaching the same file work if you try from Outlook desktop, if available?

In the meantime, I recommend the following workarounds:

• Attach the file as a OneDrive link instead of a traditional attachment. This is the most reliable method in Outlook on the web.
• Make sure the file is fully synced in OneDrive before attaching it.
• Try clearing the browser cache or using a different browser.
• If possible, try creating the meeting and attaching the file from the Outlook desktop app, which may handle attachments differently.

Using a OneDrive link ensures attendees can access the file and avoids upload issues. Please understand that our initial response does not always resolve the issue immediately. However, with your help and more detailed information, we can work together to find a solution.

I truly appreciate your patience and understanding. If you have any further questions or need further clarification, please feel free to reach out. I'm looking forward to hearing from you. 

Thank you for your cooperation.

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Answer 2

In Outlook on the web/Outlook.com, there are known limitations and an active issue with sending items that contain traditional file attachments. For calendar events, only events created by the organizer (or a delegate) can have files attached, and large or problematic attachments may fail to finish uploading.

To work around the issue and reliably include content with the calendar event, use OneDrive links instead of direct file attachments:

1. Create or open the calendar event in Outlook on the web.
2. Select Attach.
3. If the file is already in OneDrive, choose OneDrive.
   • If the file is not in OneDrive, choose Upload and share to upload it first.
4. Pick the file and select Share link.
5. The file will be added as a OneDrive attachment (a link) to the event.

Notes and tips based on current behavior:

• Some users are currently unable to send emails with attachments from Outlook.com; the documented workaround is to send the file as a OneDrive link instead of a traditional attachment.
• The size limit for an Outlook.com message is 25 MB including all text and attachments. If the file is large, upload it to OneDrive and attach it as a link. OneDrive links do not count toward the 25 MB email size limit, and the linked file can be up to 2 GB.
• Files can only be attached to calendar events that are created by the user or a delegate.

If the goal is to keep the content with the meeting while avoiding the stalled upload, using OneDrive → Share link is the supported and recommended method until the attachment issue is fully resolved.

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References:

• Unable to attach files in Outlook.com
• Add pictures or attach files to emails in Outlook