Hi Steve Shapiro
In addition to the insight provided by the AI, I would like to share that I tried to replicate your situation using Legacy Outlook for Mac version 16.109.1. In my testing, I was still able to use the Unread filter and perform searches as expected.
To better understand your situation, may I kindly clarify the following:
- Is this behavior only observed with these two users, or are other users in your organization experiencing the same situation?
- When using a new Legacy Outlook for Mac profile with only a non-affected account, does the behavior still occur?
- Is there any common pattern between the two affected users, such as the same macOS version or similar environment settings?
In the meantime, you may consider removing the Outlook for Mac application and reinstalling it using the updater.pkg from the Update history for Office for Mac - Office release notes | Microsoft Learn

As the currently available version is Outlook for Mac 16.109.02, you may also try installing this latest version to check whether the behavior continues. Many users have shared that installing from the updater.pkg can help address unexpected behavior.
I hope this provides some direction. If you have any updates after trying these steps, please feel free to share.
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