Pi hole doesn't start on boot after upgrade to 5.0

Expected Behaviour:

Pi hole starts automatically when I boot up the Raspberry Pi and continues running, reporting Active status.

Actual Behaviour:

Pi hole was working fine until I upgraded to 5.0. Since the upgrade, Pi hole doesn't start on boot. Initially, the web interface won't load. Running any pihole command (e.g. pihole status or pihole -d) starts Pi hole, and then it works normally (including the web interface) for a while. After a few hours or so, the DNS service/blocking continues working but starts reporting a status of "DNS service not running" and the web interface becomes very slow to load. I generated the debug token below shortly after rebooting and starting Pi hole while the status was still showing Active.

Edit: already tried pihole -r, but no change in above behavior.

Debug Token:

https://tricorder.pi-hole.net/jp517f3nh5

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