Thank you for posting your question in the Microsoft Q&A forum.
From your description, it sounds like Outlook or OWA searches are returning incomplete results even after reindexing the Exchange database and extending maintenance.
Here are some steps you may try to fix this issue:
1.Verify search health
Get-MailboxDatabaseCopyStatus | Format-Table Identity, ContentIndexState
Ensure ContentIndexState is Healthy.
2.Test indexing
Test-ExchangeSearch -Mailbox <test mailbox>
This verifies whether new items are indexed within roughly 10 seconds.
3.Identify unindexed documents:
Get-FailedContentIndexDocuments -Mailbox <mailbox>
If filters are missing, install the required iFilters or move the mailbox to re-trigger indexing.
4.Make sure the following services are running:
-Microsoft Exchange Search
-Microsoft Exchange Search Host Controller
-Microsoft Exchange Transport Log Search
5.In Outlook client setting, confirm Cached Exchange Mode is enabled.
I hope this helps.
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