It may sound strange to people who were born later. But in 90s these mechanisms were in infancy. It was normal for computers to auto-login and have no password at all, processes could each read entire memory on the machine. Software was cracked the moment it came out and it was assumed people bought any software because they feared legal action rather than because they had no other way to get their hands on it -- lat…
With windows specifically a factor is that it is/was almost impossible to get a computer (PC/Desktop) without Windows license. Compared to that the number of potentially illegal copies was neglectable. And even for Office it was probably better that people use a copy from dubious source than a competitor so they don't find out that alternatives are good enough.