I have found some strangeness in my "and" and "or" groups on occasion. Sometimes I have to swap them around. "and" for "or" and vice versa.

Also is it possible that your machine has not run a recon, since the update? sudo jamf recon.

Go into the details for your machine to make sure it is listing the correct version of the application for Outlook.

Could there be any other applications that have versions that match those numbers?

I don't know for sure, but it seems plausible that the JSS is reading the terms as ```
(title=Outlook AND version=14.1.x) OR version=14.2.0 OR version=14.2.1
instead of the intended
title=Outlook AND (version=14.1.x OR version=14.2.0 OR version=14.2.1)
```

Whenever possible, I try to keep mine more simple: "title=Outlook AND version is not 14.3.0" since it is less ambiguous.