Henry uses a rope launcher to get off the Prison Roof. He slides across with his hands, and the friction burns his hands. When he falls off, he is full of wounds and bruises, but alive. It appears that he is free, but as he stands in the middle of the road, the armored truck runs him over, leading to a fail.
Fail Screen Transcript
This seems awfully familiar...
- The armored truck that crushes Henry might be, ironically, the same truck he sneaked into when he got caught trying to break into the bank, which is the reason he's in prison. That also explains the fail screen transcipt.