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There is a vertical 'roof'. Uber a Demoman on 2fort and make him Detonate about 5 grenades. He'll go a little higher than the topmost roof and then stop.
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Aka Meet the Skybox.
Anyway, I don't mind who wins, because I already play Soldier a bit, and I need to brush up on my skills on the Demoman, even though I only play as the scout/sniper.