@brlittle, did anyone answer you (privately?)? I would imagine this would need to be run as a script on every login or something - maybe once per user?
This is kind of stupid but just in case anyone else is having this same problem, we dragged the Illustrator.app into Terminal to check its path and for what ever reason, the path that comes up in Terminal is:
/Applications/Adobe Illustrator CC 2019/Adobe Illustrator.app
and not:
/Applications/Adobe Illustrator CC 2019/Adobe Illustrator CC 2019.app
So in Dockutil, we entered the same path without the CC 2019 and it worked.
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