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David BarmanFlag for United States of America

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Remote Desktop 2012 - Outlook 2016 won't search the task items

I have a strange issue.  On a Remote Desktop Server (2012). In Outlook 2016, the user can search mail items but when tasks are searched no results are ever found.  I have tried re-creating the user profile.  We are in an on-premise Exchange 2016 environment.  I also re-built the search on the Exchange server.  However, the results are the same.

Any ideas?
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What is the result using OWA? Also set outlook in online mode and test again.
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I have looked in OWA.  I can't seem to find an option for search.  The RDS user is already setup in online mode.
Is the search service running on the RDS box?

Yes. The search service is running
Is Outlook 2016 fully patched to the latest version? This was an issue with certain builds in the past where a particular build would break tasks search as an example.

It is version 16.0.4266.1001
I don't see a check for updates option.
I would go here and try to update all the Office components you are using (try a test or separate server):

I have installed updates. In addition, I noticed today while working on one of the Windows 10 computers on the network (for the same user) that the same search issue exists.
Could this be an exchange server issue?
If the same user on another system has the issue, do you have roaming profiles in place? Also on that same Windows 10 computer, if you logon as another user, is the issue there? If it is, it is almost certainly something wrong on the backend (Exchange).

No. The user doesn't use roaming profiles. At this point I don't know if other users have issues
Another update.  I logged into the remote desktop server as two other users.  The first user had the same search issue in the Outlook tasks.  However, the next user I tried, I was able to search the tasks.

Any ideas?
Upon closer inspection.  It appears that the search issue is in the  "To-Do List".  If I select the user's task folder, it will search.Is there a known bug about the To-Do List?

Any ideas what would cause this?
What happens if you try with a different user?
I have tried it with multiple users and the same symptom exists.  
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