Sorry, I missed this reply. I saw your other one but I'm still unpacking it. I'm wondering if the router is the cause now.
● systemd-resolved.service - Network Name Resolution
Loaded: loaded (/lib/systemd/system/systemd-resolved.service; enabled; preset: enabled)
Active: active (running) since Sun 2023-06-25 11:40:29 CDT; 7h ago
Docs: man:systemd-resolved.service(8)
man:org.freedesktop.resolve1(5)
https://www.freedesktop.org/wiki/Software/systemd/writing-network-configuration-managers
https://www.freedesktop.org/wiki/Software/systemd/writing-resolver-clients
Main PID: 485 (systemd-resolve)
Status: "Processing requests..."
Tasks: 1 (limit: 18868)
Memory: 7.0M
CPU: 2.424s
CGroup: /system.slice/systemd-resolved.service
└─485 /lib/systemd/systemd-resolved
Jun 25 11:40:29 shraan systemd-resolved[485]: Using system hostname 'shraan'.
Jun 25 11:40:29 shraan systemd[1]: Started systemd-resolved.service - Network Name Resolution.
Jun 25 11:40:33 shraan systemd-resolved[485]: wlp59s0: Bus client set default route setting: yes
Jun 25 11:40:33 shraan systemd-resolved[485]: wlp59s0: Bus client set DNS server list to: 192.168.50.3
Jun 25 11:40:33 shraan systemd-resolved[485]: wlp59s0: Bus client set search domain list to: XXXX.io
Jun 25 12:14:41 shraan systemd-resolved[485]: wlp59s0: Bus client reset search domain list.
Jun 25 12:24:33 shraan systemd-resolved[485]: Using degraded feature set UDP instead of UDP+EDNS0 for DNS server 192.168.50.3.
Jun 25 12:29:01 shraan systemd-resolved[485]: Using degraded feature set UDP instead of UDP+EDNS0 for DNS server 192.168.50.3.
Jun 25 12:51:37 shraan systemd-resolved[485]: Using degraded feature set UDP instead of UDP+EDNS0 for DNS server 192.168.50.3.
Jun 25 15:23:58 shraan systemd-resolved[485]: Grace period over, resuming full feature set (UDP+EDNS0) for DNS server 192.168.50.3.
Note: This was ran on a client device that is expecting to use the Pi-hole as the DNS NOT the server running it.