Pi-Hole drops after a few minutes

Expected Behaviour:

Pi-Hole will drop my connection as after a couple of minutes of running. I go into Internet settings, change my DNS to my Pi-Hole's address, it will work for 5 minutes or so, then completely quit. If I reset (power off and power on) it will work. It will also work if I change internet option to automatically obtain my DNS.

Drops connection.

I have run sudo apt update and sudo apt full-upgrade. Neither fix the problem permanently.

Debug Token:

2iw2v87yqu

Your debug log shows an issue with IPv6 conectivity:

*** [ DIAGNOSING ]: Networking

[✓] IPv6 address(es) bound to the eth0 interface:
   fd51:42f8:caae:d92e::ff matches the IP found in /etc/pihole/setupVars.conf
   fe80::583e:b14c:1b69:2c9e does not match the IP found in /etc/pihole/setupVars.conf
*** [ DIAGNOSING ]: Name resolution (IPv6) using a random blocked domain and a known ad-serving domain
[✓] thoughcopyforest12.live is :: via localhost (::1)
[✗] Failed to resolve thoughcopyforest12.live via Pi-hole (fd51:42f8:caae:d92e::ff)
[✗] Failed to resolve doubleclick.com via a remote, public DNS server (2001:4860:4860::8888)

While your Pi-hole's IPv6 ULA address seems correctly configured, DNS resolution fails when using that address.

Likely, your clients won't be able to connect to Pi-hole's IPv6 address either.
Commonly, they would then fall back to IPv4, but clients with a preference for IPv6 may retry that IPv6 address in regular intervals, which may explain your observation.

Since your Pi-hole seems fully operational otherwise, DNS ports may still be blocked for IPv6.
Please verify that the firewall running on your Pi-hole machine is configured to allow DNS ports for both IPv4 and IPv6 alike.

Thank you for your response!

I'm honestly new to this, I'm jumping in, trying to learn as I go. When you say to verify that the firewall running on my Pi-hole machine is configured to allow DNS, do you mean from the actually Raspberry Pi running Pi-Hole, or from the Windows PC that is connecting to the Pi-Hole? Sorry for being kind of illiterate.. Still trying to figure this all out.

Yes.
Make sure it is allowing port 53/DNS for IPv4 and IPv6 alike, for both UDP and TCP. Depending on your firewall, this may require you to use different commands, e.g. for iptables, there is iptables for IPv4 and ip6tables for IPv6.
Have read of Pi-hole's prerequisites section for further hints on required ports and associated firewall rules.

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