It does feel like a rather optimistic reading of the T&Cs.. Do we practically believe that Hilton would upgrade Diamonds to nicer rooms even if they're not available?

On the Diamond Desk question, people have reported having highly inconsistent results for a while now. From super-stars to people who don't appear to have ever read any T&Cs. I'm guessing that it might be one pool of agents with just a specific line for Diamond access?