Not sure about IOS, but in android, for most devices, over the air updates are usually incremental: as the patch only contains the difference between the previous and immediately next build, each patch must be applied sequentially. If a user is behind on updates, this can meana pretty long reboot cycle.
Many manufacturers also post full system images as well (and sometimes make them available through the OTA mechanism as well), allowing the current version to be flashed even if the currently installed OS is outdated or missing.
Related to this, Apple are busy rolling out a new system that can update iPhones to the latest software without taking them out of their boxes. Apple Stores will be able to placed boxed iPhone on device that will talk to the phones via NFC, which will then connect to wifi to do the update.
That should mean that someone buying an iPhone that was made months ago will walk out of the shop with an up to date phone.
Apple maintains 3 delta patches for the current version, meaning you can patch up if you are 3 minor versions behind, for example the current version is 14.1.1 and previous 3 releases are 14.1, 14.0.2, 14.0.1, Apple will prepare different patches to update those 3 versions straigh to 14.1.1. Anything more than that will require a full download of the entire system image but the phone can handle it like a normal update, it just takes slightly longer time.
(This is how they implement OTA delta updates when it first came out around maybe iOS5, not sure if they still do it now.)
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