Reconfiguring skips valid SSL cert files

I've been trying to add an SSL certification to our department's GitLab EE installation, but upon putting the cert in the correct directory, a gitlab-ctl reconfigure contains this in the Chef output:

Recipe: gitlab::add_trusted_certs

• directory[/etc/gitlab/trusted-certs] action create (up to date)

• directory[/opt/gitlab/embedded/ssl/certs] action create (up to date)

• file[/opt/gitlab/embedded/ssl/certs/README] action create (up to date)

• ruby_block[Move existing certs and link to /opt/gitlab/embedded/ssl/certs] action run

• Moving existing certificates found in /opt/gitlab/embedded/ssl/certs

• Symlinking existing certificates found in /etc/gitlab/trusted-certs

Skipping /etc/gitlab/trusted-certs/gitlab_school_edu.cer.

Skipping /etc/gitlab/trusted-certs/cacert.pem.

Skipping /etc/gitlab/trusted-certs/gitlab_school_edu.pem.

- execute the ruby block Move existing certs and link to /opt/gitlab/embedded/ssl/certs

Reconfiguration Log for this is below:

1553700848.log

I've followed this guide and gone thru the troubleshooting - they're valid files, I just renamed them in an attempt that it would work.

I find that the documentation/reporting as to why they're not working is just as troublesome as the fact that they don't work. Any suggestions?