My recent experiences have been limited to being able to upgrade, on points stays, from a two queen room to a king room... sometimes.

My most memorable experience was being told that I had been upgraded from a two queen room to a two queen room on the lounge floor -- when the lounge had been long since permanently closed down. How exhilarating!

When I am a paying guest, I invariably pay for a king room. So, it is quite frustrating to see my ability to use the points I have earned initially limited to the default option of a two queen room, and then have to roll the dice at check-in.
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Has anyone had the experience of being told there were no better rooms available, and then gone onto the Hilton app to prove that better rooms were still being marketed for the duration of your intended stay?