A Follow up to this post. I've successfully gotten pihole running as a dhcp server on my home network. Ive also set a rule in misc.dnsmasq_lines: dhcp-option=option:classless-static-route,0.0.0.0/0,192.168.254.254,100.64.0.0/10,192.168.254.35. Now most of the devices (namely devices running windows and linux) are using the static route i've set without issue. However, my fire tv and roku tv seemingly refuse to be redirected.
Expected Behaviour:
I go to any IP in the 100.64.0.0/10 range and it is redirected successfully.
Actual Behaviour:
I attempt to go to a ip in the 100.64.0.0/10 range either in the amazon silk web browser or in the jellyfin client and it fails to connect.