Hi,
For your question, please ensure whether all user experience this issue or just some special account.
If the latter, ensure Outlook is selected in index, find as below:
File-> Options-> section Search-> button Indexing Options-> button Modify-> expand Microsoft Outlook
If this issue persists, please recreate index for testing. Also check the troubleshooting steps in below link:
https://support.office.com/en-us/article/Instant-Search-is-not-finding-items-1eb50282-0fa3-4a04-8db4-ee1c14fa97ab
If all user face this issue, please stop Exchange Host Search, Exchange Search service and Search Host Controller.
Then run Get-MailboxDatabase "yourmailboxdatabase" |fl name,*path*
Once the path is located you will find a folder name with a long GUID and the word Single on the end, then rename this folder as .old, and restart search service.
Give it plenty of time to rebuild then issue the command below and make sure the status of Content Index Status is seen as healthy: Get-MailboxDatabaseCopyStatus.