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NEEDS EXTENSIVE REVISION.
In the year 1944, after their father dies, Dean and Sam are left with the remains of his infantry team deep among the forests and rivers of France where it can be hard to find a way out. Supplies are running low, Axis forces are pressing in all around, and there's a plane following them.
The question of whether the pilot is friend or foe is answered when he crashes, saving Dean from an ambush, and now Dean has a choice to make. He can help Castiel and his brother get back to Switzerland, or he can press on with his father's covert mission, worries about Sam's loyalty aside—or he can go home.