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Then again, a lot of corporate software is Java or .NET, which means a much smaller porting effort. Trying to run native Windows software under Wine, OTOH, doesn't end well (in my experience).

CEO: Haven't you two heard of Wine, ReactOS, CodeWeavers?

What do you mean "all of it"?

All of the custom internal applications written over the last decade or so that provide vital business functionality, I'd have thought.

Yep. I work at a hospital so switching to Linux would impact 100% of our applications.

I understand the desire (especially on HN) to switch to Linux, but it's just not a plausible solution for most institutions. It sounds great in theory if you don't think about how all of our end user applications are running on Windows, have specialized hardware and drivers, not to mention people love the shit out of MS Office.