Hi @JustinMicheal-7973
Could you please provide more information about your environment? Such as your Exchange server version, are you having a DAG, which outlook mode are you using and so on.
For outlook cached mode, it uses windows index. And for online mode and OWA, which use Exchage search feature.
If you are using on-prem Exchange server, check the result running the command below:
Get-MailboxDatabaseCopyStatus * | sort name | Select name,status,contentindexstate
If the ContentIndexState is not "healthy" in the results, please follow the steps introduced in this article to repair this issue: Repairing a Failed Content Index in Exchange Server 2016
If your issue occurs for both scenario(outlook cached mode and OWA), potentially the mailboxes were broken in some form. You could also try moving your mailboxes to another database or server to check the result again.
In addition, we could also check if there is any error log recorded in application log.
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