The whole issue with rollover nights very confusing, and I don’t understand why Hilton doesn’t make this clearer.

You only get to roll-over nights above and beyond qualifying for your given tier, not including the rollover nights you had from the previous year. For example, in 2023 I had 73 qualifying nights…but 10 of those were rolled over from 2022. So only three rolled over into 2024, not 13. Another way to think about it is how many nights did you actually stay in a calendar year above and beyond what you needed to qualify forgetting about the rollover nights? Last year, I had 63 paid nights; that’s three more than I needed to qualify for diamond, so three nights rolled over to 2024. This year, if I only stay 57 paid nights, I will qualify for diamond again, taking into account the three rollover nights. If want to roll-over nights into 2025, I will need to have more than 60 paid nights.

Does this make sense?

The other thing to keep in mind, is that we don’t get rollover nights when dropping down a tier. If I’m diamond, and I fail to qualify for diamond by one night, i.e., I only have 59 nights, it’s not like all of the nights above Gold get rolled over. You only roll over nights above and beyond what is required to requalify for the tier you already have.