I was off of updates for a little over 2 years, stopped right before the 2020 Holiday update to avoid the UI changes and continued skipping until late spring 2023 (when they introduced the wiper speed scroll wheel controls, first compelling new feature for me in that time). Had no trouble getting back on updates, but I don't think every update will get pushed. How long have you been waiting for an update? It may take a while to get the prompt. Also sounds like they have slowed/stopped the current holiday update deployment due to some bugs so you might be just caught up in that delay??