I’d say that the ‘modern’ era of Microsoft Enshittification started with IE4 as well as Windows 98. The Channel bar put ads on the Windows 95 & 98 desktops. It was easily disabled, but even that far back, Microsoft was starting to work on making their stuff suck just that much more.

Next was Windows ME blocking DOS access, while still running on DOS, making the OS a bit … unstable, followed by your point of Software Activation in XP.

Fun fact, there were still computers being manufactured with CPUs that don’t support Windows 11 in 2020, got one of those at work that we will need to replace before then. Thankfully only one, so it’s not too big of a deal.

Just a slight correction, Vista was the last time you could split toolbars off of the taskbar like that, its taskbar was basically the same as XP still. The redesign in 7 was when we lost that ability.

Will say the docked toolbars did look significantly worse in vista as they all got an wide aero border