Hi Bill Sharp,
Welcome to Microsoft Q&A Forum! Have a good day and I hope you're doing well!
I understand how inconvenient it is when you can’t attach files, especially if you’re trying to send something urgently.
I tested this scenario in a virtual environment using Outlook for Mac version 16.103.2. On my side, when I choose Attach file > Browse this Mac, the file picker opens and I can attach files normally. This suggests the feature itself is working in the current build and the issue may be related to your specific Outlook version or local cache.
Here are a few troubleshooting steps you can try:
1. Update Outlook to the latest version: Sometimes this type of issue is fixed in a newer build.
- In Outlook, go to Help > Check for Updates and install any available updates.
- You can also check the latest version and update guidance here: Update history for Office for Mac
2. Clear the Outlook cache: A corrupted cache can cause odd behavior like buttons not responding. Clearing the cache will make Outlook re-download your data and can often resolve UI issues.
Steps here: Clear the cache in Outlook for Mac
3. Remove and re‑add your email account: If there’s a conflict or corrupted account configuration, re‑adding the account can help.
First sign out/remove the account: Sign out of an email account in Outlook for Mac
Then add it back: Add an email account to Outlook for Mac
I hope these suggestions are at least partially helpful. If the problem continues, or if I’ve misunderstood any part of your situation, feel free to reach out anytime.
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