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.
Brown hair character (Sinji) goes with Purple.
Redhead character (Asuka) goes with Red.
Blue hair character (Rei) goes with Blue. [I think that her description should be centered on her more as it looks like it's for the white haired character imo...]
I straight up forgot that the white haired character (Kaworu) existed (Had to look his name up)
At least that's if the person making the meme has watched Neon Genesis Evangelion.
I probably should re-watch the show again, it's been a very long time...