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This is really frustrating.
Check all the enemies in the map, too.
The specialist listing on the mission select means someone in the mission has that skill, there's no guarantee it's a prisoner that has the skill.
I think that perhaps you're missing him in the midst of a ton of guys. Finding someone specific is often like finding a specific needle in a needle stack. It's harder, cuz all the needles look the same.
Sort by skill on the all staff tab, then slowly go through the skills till you find him, though I'm almost willing to bet that you can't do what you want for some other reason. If you indeed extracted the Transportation specialist. That's why I said, check with the idroid before assuming he's the transportation specialist.