My server administration journey actually began with a pirated copy of Windows 2000 Advanced Server. And I don't feel bad for it, because having started very young with Windows Server has directly led to many tens/hundreds of thousands of dollars in licensing fees paid to Microsoft at my direction :)

You missed a lot of tedious reboots by starting your experience with the Windows NT family w/ Windows 2000. Windows NT 4.0 was a breath of fresh air, as far as the UI went, compared to NT 3.51, but Windows NT didn't really come into its own, in my opinion, until Windows 2000.

The tedious "re-apply the service pack and reboot" or "you thought about changing a setting, so therefore reboot" scenarios were nearly removed with Windows 2000. Having plug 'n play and hot-plug hardware work well was great, too.

I do mostly Windows, and given the option would rather keep doing so, however you just reminded me of the "fun" of writing ISAPI extensions on Windows 2000.

For those unaware of it, IIS used to execute fully on kernel level, so ISAPI extensions were comparable to device drivers, which meant any programming error would just kill the kernel, thus requiring a reboot.

So tracking down memory corruption issues on ISAPI extensions was bound to have a countless amount of reboots during the work day.

Goodness, who decided that was a good idea?!

Thr ISAPI modules don't run in kernel mode, but they're in-process with IIS (back in W2K) and it's a bit fraught.

I assumed that kernel-mode HTTP service was an answer by Microsoft to the "Tux" web server: https://en.m.wikipedia.org/wiki/TUX_web_server