To double check, I have updated my hosts file to bypass Cloudflare and I am able to establish a connection just fine, it's just Cloudflare is now refusing to connect.
Using Caddy2 as my server, have also regenerated the certificates and updated literally everything in the hopes that it is something on my end to no avail.
Other physical nodes work fine (Cloudflare is able to serve pages from them) and are accessible except for the most important one.