Part of it was that Microsoft was really more concerned with distributors selling computers with pirated copies of Windows, and they basically would activate anything if you were willing to call.

I remember doing it a few times for the "OEM" Windows XP which was cheaper but not supposed to migrate to new machines.

Thanks for that bit of background. That make sense.

I used to think that MS were probably happy with a certain amount of “piracy” (students, voluntary groups, people starting off as self-employed contractors, etc.) because it kept people in their ecosystem (using MS Office and other Windows-only software), helped reinforce the perception of Windows as being the OS for getting stuff done (either work or games) and some of these “pirates” would become future (paying) customers.