When Encryption Was a Crime: The 1990s Battle for Free Speech in Software
One of my favourite loopholes of all time, just legally and technically.  It was illegal to export "munitions" of which computer hardware such as floppy disks with bit patterns encoding strong encryption software, along with ROMs, and ASIC microcode, and the like, could be considered munitions.  This is a reasonable enough interpretation of that law, even with the US First Amendment.But in no way is a book a munition.  So the PGP source code was published on paper and mailed to Canadians, but also some in Europe (I believe?), in any case, to countries which do not have such laws applying to encryption software.  The reams were OCR'd and typed in, and then put online, where they could be freely downloaded from elsewhere in the world.  I believe this is part of why the OpenBSD project was and still is based in Canada.https://news.ycombinator.com/item?id=7885238