Thank you for this - which confirms what I had (very belatedly) worked out for myself before coming back to this thread. I was aware that rollover nights expire and hence in my case (where I had 2 rollover nights go into 2023) my total of 39 nights in 2023 was actually only 37 because 2 of them were rollover. With 39 nights, I only qualified for silver and where I went wrong is I misunderstood that the nights I earned in excess of silver would roll over to this year - 39 nights minus 2 rollover = 37; minus 10 for Silver equals 27 to roll over to this year. However no, not so - since my status at the end of 2023 was Diamond, and I hadn't reached the 60 nights required to reach Diamond again, there were of course no nights to roll over. Further, if I had reached 61 nights (say), I would not roll over 1 night into this year because my 61 was only 61 and not 59 because of the 2 rollover nights I had rolling from 2022 to 2023. Having not stayed 61 nights in 2023 but only 59, there is nothing to roll over.

I think Hilton could benefit very greatly from making this considerably clearer in their literature and on their website. A couple of simple worked examples would make it crystal clear.

In my situation, I remain Diamond until end of March 2024 of course, and I have over 600k points. So I may well choose to use those points wisely on stays in hotels where I can maximise the return (e.g. 5 nights for the price of 4 on a reward stay) and get good Diamond benefits (e.g. not in Hamptons!) But after that I'll nee to see whether it's worthwhile me continuing to remain loyal to Hilton in 2024. On one hand it'll be easier to earn rollover nights this year; on the other it will mean staying in hotels with only silver status which is hardly worth having in terms of benefits.

I'm very annoyed I didn't understand this better last year as I'd probably have found a way to make one more one night stay in 2023 to earn Gold at least.. but here we are! Hopefully this thread will help others.