Console not updating automatically

Set your console to "instant on" mode in the power settings & enable "automatic updates" then updates for your console & any games you own will automatically update.

@BC32 If I'm not mistaking, updates aren't installed automatically, they're downloaded automatically but not installed, however I think if you have the power settings set to keep ur console in standby mode that the consoles system updates will download and
install automatically, but not updates for apps.

Are you in the preview program? My mate didn't have exact same issue as you but it was downloading an update, next day it was asking him to download it again

There was a time last month they were releasing a new preview every day.

As for you O.P., they roll updates out in waves as to not stress the system. By checking manually you can bypass it.

Have you tried hard resetting via the settings option ?

Are you in the preview program? My mate didn't have exact same issue as you but it was downloading an update, next day it was asking him to download it again

The way he solved it was by deleting his gamer tag and downloading it again

Again though it wasn't same problem as you but could be worth a try, good luck!