Nest thermostat can't connect to nest servers

The issue I am facing:
I have a nest thermostat that's not working. (It can't connect to its cloud servers, with a vague message about ping timeouts to an undefined server). I suspect that the nest is caching a DNS record somewhere because when disable the pi.hole and reboot the nest i don't see any denied lookups in the logs.

I'm looking for a debugging guide that offers advice for what I should do in this situation.

Details about my system:

What I have changed since installing Pi-hole:

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