##My question:
How can I add plex.direct to dns rebinding rules in Pi-hole?
Expected Behaviour:
When connected to the same LAN as my Plex server, I am unable to make a direct connection to the service. Some Googling indicates that adding rebind-domain-ok=/plex.direct/ to /etc/dnsmasq.d/99-custom.conf of Pi-hole will solve this issue.
Can you explain what you mean by 'unable to make a direct connection'? Rebind protection just allows a DNS record to be a local IP address instead of the actual IP address on the WAN internet.
Rebind protection isn't enabled by default with Pi-hole and typically it is something that would be managed be a router. Are you using a firewall application?
Your pihole.log shows that FTL does see your additional configuration line and is using it.
-rw-r--r-- 1 root root 31 Dec 28 08:15 /etc/dnsmasq.d/99-custom.conf
rebind-domain-ok=/plex.direct/
Dec 28 08:05:43 dnsmasq[2156]: using nameserver 8.8.8.8#53
Dec 28 08:05:43 dnsmasq[2156]: using nameserver 8.8.4.4#53
Dec 28 08:05:43 dnsmasq[2156]: using nameserver 192.168.254.254#53 for domain 254.168.192.in-addr.arpa
Dec 28 08:05:43 dnsmasq[2156]: using nameserver 192.168.254.254#53 for unqualified names
Dec 28 08:05:43 dnsmasq[2156]: using only locally-known addresses for plex.direct
Dec 28 08:05:43 dnsmasq[2156]: using only locally-known addresses for onion
Dec 28 08:05:43 dnsmasq[2156]: using only locally-known addresses for bind
Dec 28 08:05:43 dnsmasq[2156]: using only locally-known addresses for invalid
Dec 28 08:05:43 dnsmasq[2156]: using only locally-known addresses for localhost
Dec 28 08:05:43 dnsmasq[2156]: using only locally-known addresses for test
What address is being returned from Pi-hole for plex.direct? I don't see where that address has been defined so I don't think there will be an answer for queries for plex.direct.
In addition to Dan's explanations, your debug log shows that your Pi-hole machine is aware of another DNS server besides Pi-hole:
-rw-r--r-- 1 root root 259 Dec 28 08:15 /etc/resolv.conf
nameserver 192.168.254.254
nameserver 172.16.0.1
search home
That 192.168.254.254seems to be your router, and routers are likely to enable DNS rebind protection by default.
So if clients would use your router for DNS, not only would they by-pass Pi-hole, but they may not be able to resolve ip.*.plex.direct domains.