Fixed it! Terribly sorry for bothering everyone. Caddy wasn’t the issue at all.
What happened was that DuckDNS had a drop out, but before I figured that out I tried to trouble shoot (including restarting my modem). This changed the IP address that DUCKDNS was looking at. I needed to just go into the modem, grab the IP and update it in DuckDNS.
Sorry for the troubles!