I stated in the OP that cloudflair HTTPS is off.

I’m not using cloudflare for the certificate. I also can’t use the cloud for certificate anyways for internal services through a loopback.

Similarly you can have SSL termination at multiple layers. That’s works I have services that proxy through multiple SSL terminations. The issue that I’m having is that the ACME challenge seems to be having issues, these issues are documented and explained in various GitHub threads, however the set of solutions are seemingly different and convoluted for different environments.

This is why I’m asking this question here after having done a reasonable amount of research and trial and error.