Need Help Troubleshooting Supervisor Crashes

I’m running a fairly-plain setup (RPi 3/64bit HassOS) and I’ve been experiencing a series of crashes of Supervisor. Lovelace UI and my automations keep working.
Usually this happens when I try to upgrade Core, no matter if this a major or minor version change (currently running core-2021.5.5).
The upgrade process times out, then I temporary loose access to HA (coaster notification pops up). Then I get access and Lovelace is responsive, I can get access to i.e. Server Controls and restart homeassistant, but I can no longer access Supervisor. Instead I’m greeted with the ‘Check the Observer/Check System Health’ web page.
Only way to fix it is by unplugging the power. After that, usually, the upgrade works without issues. Any idea where to look for the problem?

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Did you do this?

yes and I saw nothing wrong there which is why I’m posting here.

Where is this page? is this the port :4357 healthcheck?

I hope you don’t get to see it but anyway…