I used DSL back around when it was released (and 64 MiB flash drives were common) to get around my school's network filtering. I think this was one of the reasons they hired new IT staff the following year, because the technique caught on even with the non-nerdy crowd.
Yes, this brings back such memories for me too! I also used to boot from removable media to use linux on school computers. The librarian assumed I was some kind of computer hacker and reported me to the schools IT admin. I thought I was in trouble. Instead he took me under his wing and had me work with him after school on some fun projects! Really helped me understand that the skills I was learning were valuable and that I had an aptitude for it.
Kudos to the admin, that’s a much better way to handle such a situation than what I’ve sadly read many stories about, where the IT dept seemingly takes mild cleverness by students as a personal insult and punishes them.
Reminds me of cramming an installed QuakeII on a 64MB USB stick, and quickly booting it up on a few library computers when we had an hour off in high school. They blocked installers, but not 'portable' executables or network access.