Your suggestion of changing things up in my /etc/httpd.conf file did the trick! My initial version of the file, prior to initializing the account and requesting a new domain key ended up looking like this based on your suggestions:
ext_ip="0.0.0.0" #server "localhost" { server "git.example.com" { listen on $ext_ip port 80 # serve the cgit static files directly location "/cgit.*" { root "/cgit" no fastcgi } location "/.well-known/acme-challenge/*" { root { "/acme", strip 2 } } # cgit CGI location "*" { root "/cgi-bin/cgit.cgi" fastcgi socket "/run/slowcgi.sock" } } After I was able to successfully run # acme-client -vAD git.example.com I modified /etc/httpd.conf to: ext_ip="0.0.0.0" #server "localhost" { server "git.example.com" { # listen on $ext_ip port 80 listen on * tls port 443 tls certificate "/etc/ssl/git.example.com.fullchain.pem" tls key "/etc/ssl/private/git.example.com.key" # serve the cgit static files directly location "/cgit.*" { root "/cgit" no fastcgi } location "/.well-known/acme-challenge/*" { root { "/acme", strip 2 } } # cgit CGI location "*" { root "/cgi-bin/cgit.cgi" fastcgi socket "/run/slowcgi.sock" } } server "git.example.com" { listen on * port 80 block return 301 "https://git.example.com$REQUEST_URI" } The site now gets an "A" grade over at ssllabs.com. I guess my only remaining question is how did you know I needed to make this change? I know the OpenBSD documentation is really good but I'm still fascinated how people manage to sort things like this out. Maybe it's just pure experience? Either way, thanks again! Samir This e-mail, and any attachments are strictly confidential and intended for the addressee(s) only. The content may also contain legal, professional or other privileged information. If you are not the intended recipient, please notify the sender immediately and then delete the e-mail and any attachments. You should not disclose, copy or take any action in reliance on this transmission. You may report the matter by contacting us via our UK Contacts Page<https://www.nationalgrid.com/uk/contact-us/> or our US Contacts Page<https://www.nationalgridus.com/contact-us> (accessed by clicking on the appropriate link) Please ensure you have adequate virus protection before you open or detach any documents from this transmission. National Grid plc and its affiliates do not accept any liability for viruses. An e-mail reply to this address may be subject to monitoring for operational reasons or lawful business practices. For the registered information on the UK operating companies within the National Grid group please use the attached link: https://www.nationalgrid.com/group/about-us/corporate-registrations