@ Sanditz
Well that's much different from when I was involved then. Win95/98 didn't come in Home and Professional versions and Win9x was the standard desktop OS. Those Win95 licenses were certainly not upgrades for machines running Win3.11 because those machines were never available with Win3.11.
I suppose WinNT4/Win2k could be construed as a professional upgrade to Win95/98, but I rarely saw them on corporate desktops and given the small numbers involved when I did, unlikely to have been Volume Licenses.
Also I attended a Tech Briefing on MS licensing changes in 1997, a memorably boring event. I suspect I would have recalled this requirement of effectively purchasing two licences per machine had it been mentioned. I would have been appalled.
The free breakfast was very nice; I recall that. And the free copies of version 8 Corel Wordperfect Suite, CorelDRAW! and Wordperfect for Linux. Sadly, the copy Ventura Publisher was a timeout demo only.
How times change...