Hello @Observebreathe,
I believe you have some Geo Blocking happening for HTTPS on Port 443
As seen here, Permanent link to this check report, several places around the world are getting "Connection timed out".
Let's Encrypt uses Multi-Perspective Validation Improves Domain Validation Security - Let's Encrypt
These happen from multiple Geos around the world and can change at anytime.
Please also read these:
Edit:
I forgot to mention there is a redirect from HTTP Port 80 to HTTPS Port 443 happening, which is fine; but the redirection also must not be blocked.
curl
$ curl -Ii http://observebreathe.com/.well-known/acme-challenge/sometestfile
HTTP/1.1 301 Moved Permanently
Server: nginx
Date: Sun, 08 Dec 2024 18:33:09 GMT
Content-Type: text/html
Content-Length: 162
Connection: keep-alive
Location: https://observebreathe.com/.well-known/acme-challenge/sometestfile