It does make it to the server, but it doesn’t get content and only a 404. This is something you need to fix on the server.
I would suggest you pause Cloudflare and talk to your host to make sure everything loads as desired on HTTPS. Once everything works, it will also work on Cloudflare.
@sandro , I did this. The host is sitting under my desk with the local network hostname “piguy”. http://piguy and http://highhands.piguy both work as expected. My server listens on port 8080, so I ran sudo tcpdump -i any port 8080 -n to monitor traffic and I see traffic from Cloudflare when accessing the main site, but no traffic when accessing the subdomain. At this point, if we assume Cloudflare is properly forwarding traffic, there might be some setting on the TLS setup I might be missing?
Hold on, that doesn’t match what I am seeing. My server is definitely listening on 8080, I’m able to see the main site through Cloudflare, and with tcpdmp, I also see the TLS daemon forwarding traffic to 8080 like it is configured to do.