HTTPS push - OpenSSL error, or API unreachable

Hello community,

I setup a gitlab instance in a FreeBSD 11 jail and it appears to be up and running without issue. I have enabled HTTPS using LetsEncrypt certs and that is working in my browser.

I setup an initial project, cloned it successfully from a different WEB jail, but when I try to push my README file I get the following error:

$ git push -u webjail master
Password for 'https://malnpr0@git.someguy.tech:443': 
Counting objects: 3, done.
Writing objects: 100% (3/3), 222 bytes | 0 bytes/s, done.
Total 3 (delta 0), reused 0 (delta 0)
remote: /usr/local/share/gitlab-shell/lib/gitlab_net.rb:226:in `add_file': system lib (OpenSSL::X509::StoreError)
remote:     from /usr/local/share/gitlab-shell/lib/gitlab_net.rb:226:in `cert_store'
remote:     from /usr/local/share/gitlab-shell/lib/gitlab_net.rb:157:in `http_client_for'
remote:     from /usr/local/share/gitlab-shell/lib/gitlab_net.rb:188:in `request'
remote:     from /usr/local/share/gitlab-shell/lib/gitlab_net.rb:217:in `post'
remote:     from /usr/local/share/gitlab-shell/lib/gitlab_net.rb:36:in `check_access'
remote:     from /usr/local/share/gitlab-shell/lib/gitlab_access.rb:30:in `block in exec'
remote:     from /usr/local/share/gitlab-shell/lib/gitlab_metrics.rb:47:in `measure'
remote:     from /usr/local/share/gitlab-shell/lib/gitlab_access.rb:24:in `exec'
remote:     from hooks/pre-receive:19:in `<main>'
To https://git.someguy.tech:443/web/web-jail.git
 ! [remote rejected] master -> master (pre-receive hook declined)
error: failed to push some refs to 'https://malnpr0@git.someguy.tech:443/web/web-jail.git'

I suspect it’s breaking because of this:

OpenSSL::X509::StoreError

I also suspect that the issue is related to the gitlab-shell configuration and my CA or cert/keys. Despite specifying the CA_file or CA_path the issue still presents. If I reference something other than the CA (such as the key in the CA_file path) I see this error instead:

$ git push -u webjail master
Password for 'https://malnpr0@git.someguy.tech:443': 
Counting objects: 3, done.
Writing objects: 100% (3/3), 222 bytes | 0 bytes/s, done.
Total 3 (delta 0), reused 0 (delta 0)
remote: GitLab: Failed to authorize your Git request: internal API unreachable
To https://git.someguy.tech:443/web/web-jail.git
 ! [remote rejected] master -> master (pre-receive hook declined)
error: failed to push some refs to 'https://malnpr0@git.someguy.tech:443/web/web-jail.git'

This further confirms in my mind that the issue is tied to gitlab-shell is some way since modifying the configuration file changes the results of that push. I’m at a loss currently…I keep poking at it but figured I’d post here in in the mean-time. Any and all responses are greatly appreciated!