Problems with incomplete Search results in Outlook 2016

Several months ago, we migrated from Exchange 2007 to Exchange 2013.
Shortly thereafter, we did a PC refresh and went from WIN7 Pro 32-bit  to Win10 Pro 64-bit.
We also upgraded from Office Suite 2010 to 2016

Search results within Outlook 2016 are hit and miss for 90% of our users.  When searching, there are items missing from the search results.
Some people have the issue searching their emails only, some their calendar appointments only, most have incomplete search results of any type.

All machines are built/configured the same.  We've rebuilt the indexer, we've tried being in and out of Cache mode, We've tried toggling all the various Search options to no avail.  Now I have some users that claim their searches work properly every time.  But they don't have the volume of some that are having the problem.  We've compared settings and made them identical, to no avail.

The only real pattern I can confirm is that anything that was there prior to the migration shows properly in the search results.  Even calendar appointments in the future.  But anything added since we started using Outlook 2016 seems to be the hit/miss piece of the puzzle.
Indexer always says it is complete.  We included every possible location in the indexing option sources to search.

We can see an entry on the screen in the calendar or an email in the inbox that will not show up in the search results.

Any ideas or suggestion on what else we can try?  What we're overlooking?  Have tried reaching out to Microsoft on several occasions, but so far, they've been of no help.   I suspect it's a Microsoft bug.  Seeing way too many posts online around the world of others having the same type issues.

The masses are extremely frustrated and ready to go back to the old platforms.

Any ideas or suggestions would be greatly appreciated.
Melvin EvansDirector of Information TechnologyAsked:
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Simon Butler (Sembee)ConsultantCommented:
If you do a search through OWA, does that show the full results?

Simon.
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Melvin EvansDirector of Information TechnologyAuthor Commented:
Same results in OWA, but it appears that if a user searches from their iPhone (ActiveSync) the search is complete.
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Simon Butler (Sembee)ConsultantCommented:
ActiveSync doesn't use the Exchange search index, it uses local information and a direct search of the mailbox. Therefore the fact that it works in ActiveSync is meaningless.

However if you are getting the same (Wrong) results in OWA, then unfortunately it would appear your search index is still not correct. You will need to reset it again and let it rebuild. If you have multiple servers then you need to do the reset on them all.
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Melvin EvansDirector of Information TechnologyAuthor Commented:
Sorry for the delay and thanks for the insight.   We rebuilt the content index on all exchange servers and once they were all healthy, the problems were resolved.  We had to rebuild one database in particular several times before it became healthy, but it finally worked.

Some servers have multiple databases, which is why it appeared to work correctly for some and not others.

Thanks!
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Melvin EvansDirector of Information TechnologyAuthor Commented:
I already confirmed that Simon's answer was correct.
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Simon Butler (Sembee)ConsultantCommented:
The asker confirms that my answer was correct.
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