Thanks again Matt.
I tried that and still no luck, then it occurred to me that this might be an issue with my AWS Global Accelerator. https://aws.amazon.com/global-accelerator/
Here’s my findings.
If I forward my domain directly to the Caddy server it does forward correctly to HTTPS. However if I forward my domain to the static IP address on my load balancer, that doesn’t seem to forward to https. Clearly not an issue with Caddy.
Here’s a screenshot of the network tab for these requests. I don’t see the “server : Caddy” in the header, I guess that means it’s not even hitting the Caddy server.