Hi jrauman,
What's the version of your Outlook? (File > Office Account > About Outlook). Please make sure you have upgraded your Outlook to the latest version.
>>Outlook will fail to display search results. If i clear the search criteria and try again, it works fine. Only a problem recently.
Do other users in your working environment have the same issue as you?
I tested a lot in my environment(Version 2001 Build 12730.20430) but could not reproduce this issue so far.
Since you have mentioned that this issue is only a problem recently, there might be something related to the Outlook version which may cause the issue. Please try upgrading your Outlook to the latest version and see if there is any difference.
Besides, as I know, Outlook search feature is based on windows search, it is suggested to try to rebuild the search catalog via Windows control panel > Indexing Options > Microsoft Outlook > Advanced > Rebuild and see if it works.
Hope this can be helpful.
Regards,
Jeff Yang
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