Anecdotally, I've done work with a few medium-sized businesses around updating legacy business critical apps now and in at least one case the app just wouldn't

Anecdotally, I've done work with a few medium-sized businesses around updating legacy business critical apps now and in at least one case the app just wouldn't run on Windows 10 at all but worked fine in Wine with no special configuration. Microsoft appears to have taken a step back from their long-held focus of not breaking things on upgrades. Granted, these clients should not be using Win9x apps still and hoping for compatibility.