The issue I am facing:
When enabling the DNSSEC option in the Pi-Hole web interface, the Cloudflare Security Check is no longer able to verify that I am using Secure DNS. With this option disabled, I get green checks for everything (except Encrypted SNI). When enabling this option, I get a yellow X for Secure DNS.
Details about my system:
All software versions are current as of this writing. Running Pi-Hole on DietPi 32bit on a RPi 2B. Pi-Hole is configured as my DHCP server.
What I have changed since installing Pi-hole:
Installed dnscrypt-proxy according to the Wiki guide. Using the 'cloudflare-family' server, set 'require_dnssec' to 'true', and set the dnsmasq 'proxy-dnssec' option.