In 2016 I was asked to install some software on a WinSvr2012R2. I was forced to install it on my Win8.1 tablet first, because the 16-bit stub didn't work on x64 2012R2. After install I copied the files to the server and the software brazenly showed "XXX for Windows 95" in the Help->About. On a 2012R2 x64 server. In the year 2016.

There was (and is) a lot of shit which developers did wrong (including writing directly to C:\WINDOWS). Yet if they did stick to the basics (GDI output and so on) that worked for decades. I abandoned Corel PhotoPaint 3 (with (c) 1992) only after moving to Vista in 2008.