I still like the one when ubuntu devs decided that netcat's behavior to keep the connection open and wait for the answer when connecting to a port is outrageous and closed the connection after sending the request. We used netcat to debug network connectivity. The day I learned that I cannot trust any piece of software that is part of ubuntu. Later the also pretty good purify complains bug followed. Those guys might have been the Debian folks.
Because Ubuntu included proprietary drivers by default, notably ATi and NVIDIA and Wi-Fi cards, all of them were so tedious to install on Debian (which was one of the most popular Linux distributions at the time)
It also shipped latest free software from two months ago (GNOME, X) that actually worked on a 6 months schedule! (Remember Debian releases back in the day? If you attempted to get your USB flash drives to just work, you'd otherwise be recompiling half of your system and Gnome with Garnome or jhbuild)
And it shipped actual, physical CDs across the world for free. It was 2004!
Then it shipped a free LTS that may not have been as stable as RHEL, but it was definitely fresher and with guaranteed updates (for main) for 5 years (3 on desktops early on). It was 2006.
