600+ nights in the last 7 years. Been officially upgraded 7 times.

Most recently at a Waldorf, I knew they had availability at check-in. I didn’t mention or ask for an upgrade. The front desk agent said “thank you for your diamond status. (Sigh) we tried very hard to upgrade you but there’s nothing available.” It was a weak attempt to sound like they really exerted themselves to do me a favor.

I got my 2 bottles of water. After checkout, I had to call the accounting office to get my F&B credit per the T&Cs.

Lots of places do the “executive floor” thing where you’re upgraded from a 1K room on the 9th floor to the exact same room on the 10th (but executive) floor. Absolutely no difference, but the new room has a “Hilton” logo next to the number on the wall.

Long story short, if OP wants a suite, book a suite. It’s on you to make sure you get the benefits you’re entitled to.