This is not a new problem. I worked in corporate IT in the early 2000’s. Both attitudes existed even then, though of course there was no App Store back then. Nevertheless there was a strong preference among younger employees for paid software—the kind you get in boxes. The older generation viewed most software as suspect, but were willing to accept “official” solutions from Microsoft and other name brand software vendors. It seems comical now, but at the time Red Hat was viewed almost universally among my coworkers as a terrible idea. And forget about custom software. Rolling one’s own software was widely seen as crazy talk.
Never underestimate the blame game. It's a lot easier to place the blame on MS than on your own organisation. All customers knows you can't do anything about how windows works and have accepted the dysfunction already.
Already in the 90‘s I has advocating for FOSS in a big company. And someone told me “nobody was ever fired for buying IBM” that phrase was already very old…
I remember buying SuSe Linux as literally boxed software around that time. But I bought it for my own use and my employer (not software industry) was running mostly windows with some legacy Unix.