It was 2006 or 2007 when I sent a girl from my class a funny pdf.exe on ICQ, which simply restarted her computer when she started it. I didn’t know that she would lose a whole day’s work that way, but eh what are you gonna do if programs don’t have autosafe.
Also, anyone remember “dialers”? Fun times.
Then again, I’m not sure if for servers, Debian is still as important as it used to be. I’m probably overly generalizing, but often all you need is a few daemons installed natively (SSH, Docker, firewall), and your reverse proxy and any services are then managed e.g. via docker compose.
There are variations on this, but with the fraction of packages installed via the distro’s package manager having become smaller like that, what distro you use for a server should not impact your QoL as severely as it used to I think.
Your point about desktop usage still holds of course.
I didn’t even know about libredirect :)