Hi @Bradley_Street,
The update did actually run. Each time you pressed Update this evening, the computer was rebuilt and your files carried over, which takes a few minutes. The button showing up again afterwards looks like a known issue where the app keeps offering Update even after one has finished. There’s no need to keep pressing it.
One of your tries ran right after the computer woke from sleep and was skipped because its files weren’t saved yet. Nothing was changed by that one.
The “Grok Bot’s computer is asleep” note belongs to the Route traffic through this computer setting. It just means the computer was sleeping at that moment, and routing reconnects when it wakes.