It would have been relatively straightforward for Microsoft to support 16-bit on 64-bit, but they decided not to. I can't help but feel that that is just more evidence that whoever is running Windows development these days hates everything that used to make it a good desktop.
64-bit Windows has never supported 16-bit. This has nothing to do with "whoever is running Windows development these days"
Back when 64-bit Windows came out (with XP and Server 20003), the adoption was pretty small since most applications were not 64-bit and did not need 64-bit address spaces. Microsoft saw the opportunity to kill at least one backward compatibility burden by not even trying to support 16-bit for x64. They figured, rightly, that by the time x64 became widespread, 16-bit would be obsolete.
> This has nothing to do with "whoever is running Windows development these days"
> Microsoft saw the opportunity to kill at least one backward compatibility burden by not even trying to support 16-bit for x64.
These two statements are at odds. Microsoft used to take compatibility extremely seriously. It would have been relatively trivial to allow 16-bit applications to run, and obviously there is desire to do so since WineVDM exists, they just arbitrarily decided not to.
I suspect this is because they've become infected with developers who use Linux a lot and think nothing of breaking compatibility every release, let alone in cases like this.
Virtual 8086 mode was gone, but they could have just emulated it. The real reason 16-bit apps don't run is Microsoft didn't think it was worth the effort.
Wasn't 64-bit windows 2k/64 itanium-based, not x86-based? If so it would have required supporting existing binaries compiled for a different architecture. My understanding is that the only 16-bit support in 64-bit windows is a few specific loaders for things like 16-bit installers (please correct me if I'm wrong)
Yes, the initial 64-bit OS was IA64 and that was the perfect excuse to dump NTVDM, instead of trying to do a W16OW64 or something of that sort. x64 XP and 2003 further solidified that decision because they were "professional" SKUs and Microsoft could dictate that they didn't care about DOS/Win16 for the "new" platform.
[0] https://github.com/otya128/winevdm
It would have been relatively straightforward for Microsoft to support 16-bit on 64-bit, but they decided not to. I can't help but feel that that is just more evidence that whoever is running Windows development these days hates everything that used to make it a good desktop.