Partially, yeah. I do feel a bit sorry for him. Someone who does something that stupid has, I assume, been denied even the barest modicum of real parenting. It's easy to imagine some idiot who thinks that the rules are something to be laughed at and flirted with doing this. It seems a little harsh to go from one extreme of almost zero consequences to the other extreme where you're essentially putting someone in a concentration camp for (maybe) nicking your flag.
All of which said, though I feel a bit sorry for him and wouldn't go out of my way to punish him if he got out, I probably wouldn't bother getting someone who thinks it's a bright idea to go to the DPRK back either. Like, 'you put your testicles in a crocodile's mouth, I feel sorry for you but I'm not paying your medical bill.'
There's a story called The Cold Equations which... a lot of people take away from that Heinlen's perspective: "The only universal capital crime is stupidity. The punishment is death. There is no appeal." (IIRC, it was something along those lines.) But I take a different view of it - that the girl hadn't been adequately warned because she had likely lived in an environment where the warnings were misused, where there were little to no consequences for violating them.
That determines a lot of my sympathy. If someone can reasonably be expected to know....
In this case, I largely think that someone could reasonably be expected to know that going to the DPRK was not a bright idea. Still a bit harsh, mind.