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Recently I suffered from not getting the “space available” upgrades during my last 4 stays at London Hilton group properties which is one of the supposed perks of diamond membership.
A month ago I overheard a fellow diamond member on a car hire shuttle bus do the following. He made 2-3 bookings at his favourite Hilton properties in London for the same stay and then called his preferred property at 11am and asked what room he had been allocated. If he was not upgraded, he called the next one and so on.
Whichever was the best, he travelled onto and checked in, cancelling the others before the cut off.
Am not sure, I have the time to do this but it was effective and something I might try if the next time I am told “No upgrade ‘coz we are full, Guv”