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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

I like it too, but I'd also challenge even this:

> This is a reasonable enough interpretation of that law, even with the US First Amendment.

I don't think it's reasonable at all to call computer code anything other than speech. In fact, just like you say, you can write it in a book. I'd go one step further and say, "if you can encode it in a book, it's speech and therefore protected expression, and cannot be banned." (I am aware that is more permissive than current US laws - I think illegal numbers is a thoroughly Wrong and unconstitutional concept).

That simplistic and fundamentalist interpretation is incompatible with copyright, publication of trade secrets, classified information, invasion of privacy (nude pics), distribution of pedophilia materials, etc.
I would rephrase your first part as: copyright and government protection of trade secrets is incompatible with a principled (n.b.: not "simplistic") view of freedom of expression.

As far as the other acts that rode along on the coattails of your comment: there's no reason the production of that material couldn't remain illegal in this hypothetical.

> That [...] interpretation is incompatible with [infringments against free speech].

Yes. Yes it is. That's the point.

Do you not think there should be restrictions on free speech?
Why should there be?
Because CSAM is bad, copyrights are important, etc.
Libertarian reasoning circa 2005: all digital files are just numbers; you can't patent mathematics; therefore download all the movies illegally!
Have you considered the possibility that the urge to censor is the issue there?
Have you considered that the enforcement of copyright, trade secrets, and state secrets are incompatible with freedom of speech?
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Yes, and I think this is more obvious today, but in the early 1990s printing it on paper proved the point very clearly. "Software" still has a certain mystique about it even today for non-tech people. But it's just something you could print on paper and type back in.
Do you think the US military doesn't understand the concept of secret papers?
There's a history of restrictions over specific information, including specific numbers and quantities, or descriptions of items.

We know most of them through exception --- casses in which restrictions were ultimately overcome (the 1979 publication of schematics for a hydrogen bomb by Progressive being a notable instance: https://www.washingtonpost.com/archive/politics/1979/03/10/m...)

Free speech is an ideal, not an absolute. There are considerations under which speech can be and is restricted. Those boundaries shift with time, and specific decisions may later be found inspired or wanting. It's a genuinely complex domain, and simply declaring "free speech" is nowhere near sufficient in addressing the questions raised.

That was the model for my favorite product I worked on. Search for SUNW and ELVIS. Passion product for Scott.
While this actually happened, was it ever challenged in court? Because judges aren’t robots, and I find it highly unlikely that they would interpret so literally as to allow this loophole.
This is good, but it entirely omitted the contribution of Dan Bernstein, who was the one who actually fought the court battle (initially with the help of John Gilmore and the EFF).
Exactly. djb gave us so many gifts. Encourage everyone to checkout https://cr.yp.to which is his site with all his software like mail and dns servers, ciphers, etc. you have used before.
> The NSA made the public case that Zimmermann's software would be used by child molesters and criminals.

They use this as a foot-in-the-door then, and they use this now.

> The NSA made the public case that Zimmermann's software would be used by child molesters and criminals.

Drug-dealers, money-launderers, terrorists, and pedophiles:

* https://en.wikipedia.org/wiki/Four_Horsemen_of_the_Infocalyp...

Incidentally, the same reason Apple thinks cryptographic privacy without spyware backdoors is unacceptable.
Can't say much but recently I stumble upon data about crypo laundering investigations. I don't know how to feel about all this.
If encryption is a weapon, give me the 2nd Ammendment.