When I crossed Turkmenistan we took usual route Ashgabat-Dasoguz. We got GPS tracker and on border they drew the way which we have to take (approximately). We were wondering around and sightseeing Ashgabat, did gas crater. In 4 days we didn't see any police checkpoints, at exit I just gave them GPS tracker, nobody checked anything.
Honestly, I didn't even feel that GPS tracker is working. I've heard some people never even plugged it in.
I think that worst that can happen is police checkpoint turns you around if you are sticking to main roads. I don't know what would happen if you by mistake drive into some military/oil zones, I wouldn't recommend driving on random unmarked roads too far off.
All about Turkmenistan
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