He wanted his Adobe to work and it was my job to make it work.
What happened when you attempted to recreate the problem on another system?
I assume when you talk about being a pain in the arse to support
that you have more than one client using Adobe software. And that finding the root of the issue would be important enough to recreate the issue to find a solution that doesn't require toasting all your client's systems every time an issue with an application arises.
I find it both hard to believe and a little sad that Adobe products work so poorly on Windows. I was under the impression that Adobe considered the Windows platform quite important.