I'm thinking of the transitions from Windows 3.1 to Windows 95 (IIRC introducing 32-bit and filenames longer than 8 characters) and the transition from Windows

I'm thinking of the transitions from Windows 3.1 to Windows 95 (IIRC introducing 32-bit and filenames longer than 8 characters) and the transition from Windows 95 to Windows XP (IIRC introducing a proper permission system, thus breaking anything that relied on being able to write things outside of user-owned folders) I agree they were famously accommodating in those days. But they also had enough market power that if they said users could only write to one folder and it had a space in the filename, developers who disliked it couldn't vote with their feet.