We were with convoying Mongolia with bunch of cool guys from AUS, NZ and UK. One team went through northern Iraq (it was relatively safe back in 2011) and later had to double as Kyrgyz emergency as they were driving an ambulance. Links are mostly broken, but you can read some of it here:
https://web.archive.org/web/20111122143223/http://www.travel...
We had another trouble in Novokuznetsk, as we were filming clip on factory there, for a project on environment and pollution. Part of the sponsorship deal, so we took Wikipedia and found bad spots along the route. Of course, few minutes after setting up the camera we were busted. Screeching tyres of UAZs as they were coming out, like in the movie. It was tense, but we played Slavic card there and so they just deleted memory cards. At that point after 30 days or so in a van, I guess we were not much of your typical spy. :). We were told it's good it was private security company, because they could just kick us out from the scene without all the paperwork required by regular police.
Good times :)
http://settledforthis.blogspot.co.uk/2012/09/mongol-rally-1-...
In fact, if you need to spend a month in a car, it might be better with a person you don't know (friend, relative...). There will be too much information you don't need to know. :)
Another #protip: the ultimate "get out of jail" card is the red MAN UTD t-shirt.
It's the better universal value than cigarettes, pens or crisp $20 notes. If we had few of those (fakes, obviously) we would've seriously cut our mechanic bills and few other expenses along the way.