Just had to hard reboot Pi after upgrade to 2021.5.5 stalled

I have a Pi3 running a supervised install of 2021.4.4. It’s a subsidiary HA install and only has ZWave and Zigbee devices attached to it. It’s a supervised install so that I use the LiFEPO4wered UPS driver to shutdown gracefully if power fails.

I went to upgrade to 2021.5.5 a while back and left the machine whilst I had lunch. Came back 90 mins later to find the upgrade (apparently) still running. Could ping the Pi but not SSH in. Even the UPS driver failed to shut the Pi down when I pressed the shutdown button. So I had to hard reset.

Luckily the Pi came back up in 2021.4.4 but it’s left me nervous to try the upgrade again.

Has anybody seen anything like this?

Unfortunately I just experienced something worse. This morning when I tried to connect to HA I couldn’t.
I did upgrade 20 2021.5.5 yesterday but after the upgrade I had HA running. This morning however there were no response.
I’m running HA on a Raspberry Pi4 with 8GB of RAM and I run it from a SD card. My first thought was that the SD-Card had gone bad but I was still able to ping the Raspberry and I was still able to mount it on my iMac and browse the file-structure in the Config folder. I did try a brutal power cycling of the Raspberry but without any changes. I still can’t connect to HA but can still mount and browse the files.
As far as I can tell nothing in the Config file get’s touched after the power cycling so I’m guessing that HA doesn’t get very far.
Any ideas or suggestion on how to troubleshoot this problem?
(I do have a recent backup and extra SD cards but would prefer to figure out what caused this before destroying the evidence)