SSLError: _ssl.c:489: The handshake operation timed out
A lot of these in your logs. My guess, since this is using the long-obsolete Python-based webui (that doesn’t change any more, at all), is that it went bad after a system upgrade.
The Python-based webui relied on very specific versions of Python’s SSL module, which was broken in newer versions (regression!). The answer likely is you need to downgrade these versions, a process outlined in this URL: