Custom ROM gang: puts off updates for three months because you can't be bothered to actually download the package and re-flash it manually, and it might also screw up your user data and require a reinstall
Granted, this used to be a way bigger problem in the Kitkat/Lollipop days, when CyanogenMod hadn't become Lineage yet. Nowadays OTA updates work pretty well, but occasionally it'll still tell you to flash it manually.
I have a MacBook for work and I'm not sure it has ever updated overnight like it said it was gonna. It's quite annoying because OS X updates (or my work's custom stuff? Idk) are so, so bad. Big, focus grabbing prompts popping up to say I need to update, when I agree to do it, it has to download too (every other system I use just downloads automatically and only prompts about the restart), and it is the slowest OS update to boot!
The annoying thing to me is my watch. I wear my watch to sleep because I like to track my sleep and I like waking up to the vibration as opposed to noise. I have auto update on for my watch but it only will do it in the middle of the night while on the charger. I can’t tell it to do it mid-morning instead. So I always have to remember to manual update after putting it on the charger in the morning.
That's so frustrating. Smart watches seem to be in such an experimental place still.
I think it often does this when you have an alarm set. It doesn’t want to update, then break and have you sleep through whatever time you set to wake up