Hello Rebecca Thompson,
Welcome to the Microsoft Q&A forum. I understand how frustrating it can be when attachments fail to download, especially after you’ve already tried restarting the browser and clearing the cache.
I noticed there is already a Q&A Assist response on this thread. The suggestions provided there are generally correct, so I would recommend trying those steps first if you haven’t already, particularly checking browser extensions and confirming there are no temporary service issues.
That said, I’d like to add a few additional points specific to Outlook on the web on macOS using Chrome, which often help in this situation:
1, Check Chrome download and pop‑up behavior for Outlook on the web
In Chrome, attachment downloads in Outlook on the web rely on pop‑ups and redirects.
- Open Chrome Settings > Privacy and security > Site settings
- Review Pop‑ups and redirects and ensure they are allowed for Outlook on the web
- Also check Downloads in Chrome settings and make sure Chrome is not set to block or prompt in a way that prevents downloads
After changing any settings, refresh Outlook on the web and try downloading the attachment again.
2, Test in a Chrome Incognito window
This helps rule out cached session data and extensions without changing your main browser setup. If downloads work in Incognito mode, the issue is very likely related to extensions or stored browser data in your regular profile.
3, Temporarily disable Chrome extensions
Some extensions - such as ad blockers, download managers, security tools, or password managers - can interfere with attachment downloads in Outlook on the web.
Go to chrome://extensions > Temporarily disable all extensions > Restart Chrome and test the download again.
If this resolves the issue, re‑enable extensions one by one to identify the specific conflict.
4, Test with another browser on the same Mac
This helps determine whether the issue is Chrome‑specific.
- Sign in to Outlook on the web using Safari or another browser
- Try downloading the same attachment
If downloads work in another browser, the issue is isolated to Chrome rather than Outlook on the web or the mailbox itself.
5, Confirm whether the issue occurs with all attachments and all senders
This helps narrow down whether the problem is session‑based or mailbox‑specific.
If the issue persists after trying both the Q&A Assist suggestions and the steps above, please let me know which step changed the behavior (if any), or whether you see a different message. I’ll be happy to help you narrow it down further.
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