Hi @John ,
Before going further, please make sure you have upgraded your FSLogix and Outlook to the latest version.
According to your description, seems that your issue might be more related to the specific FSLogix environment and I'm afraid that Troubleshooting methods used in windows environment might not help much. I did some search about your issue and found a Troubleshooting Guide related to similar issues as yours in FSLogix forum. Please check if they could be helpful to your issue:
Outlook Search Troubleshooting Guide
Configure Profile Container to roam the Windows Search database
Besides, you might need to first check the capabilities of your environment, just as the official document mentioned:
Changes to enhance native search behavior in Windows Server 2019 and Windows 10 multi-session remove the need for FSLogix search functionality. FSLogix search functionality is not compatible with Server 2019, Windows 10 multi-session, and subsequent multi-session operating systems with enhanced native search capabilities.
Hope this can be helpful.
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