Can a scenario before a question even be a strawman? (And yet you chose to dodge the question; one gets to wonder why; “it wasn't for me” won't do, for you chose to answer the post anyway ;-)
Anyway, your situation is not hypothetical. It was real for me. What did I do? Implement a Free Software version of the government-supplied software. http://fsfla.org/~lxoliva/snapshots/irpf-livre/ *while* fighting the obligation to use the government-supplied software in court.
Now, as for strawmen... How exactly does Debian's refraining from distributing any particular piece of non-Free Software land you in jail? Surely you're not saying than when people become Debian users they become incapable of finding, installing and using software that is not in Debian repositories, as in, if it's not in a Debian repository, it doesn't exist. (nevermind the doublethinking on whether or not nonfree is a Debian repository :-)
Why oh why, if you chose to use the government-supplied non-Free program, wouldn't you install it from the government site, like everyone else presumably does, or perhaps from some repository *truly* external to Debian (maintained by Debian fans that happen to live under the same authoritarian government)? How do you turn that into a requirement for Debian to contaminate its repositories with non-Free Software, betraying both of its primary goals (freedom and users)? How does your strawman feel now? :-)