About 10 years ago I knew another Canadian who crossed China-Laos-Thailand-Malaysia without a valid passport or visa (or pretty much any money whatsoever). This was after about 3-4 years in China with an expired visa. When you consider how short the Thai/Malay land border is in particular, if it's possible there, then it would appear that most borders are not very well controlled. This accords with my own experience visiting land borders in remote areas and speaking to local inhabitants (mostly China-Burma-Laos-Vietnam but also Algeria-Tunisia). Allegedly he turned himself in at the Canadian consulate and was flown home.
I am curious, do you mean he by some means simply managed to get border control to let him pass through, or he crossed the border without being controlled? E.g. crossing through sparsely populated areas / nature?