I'v set up transmission behind a secure reverse proxy, which is Apache with Let's Encrypt. Over HTTP this worked a charm. Now with HTTPS the web interface works perfect, but the GUI cannot connect to it:
error:140770FC:SSL
routines:SSL23_GET_SERVER_HELLO:unknown protocol
Looking at the results from an ssllabs security report I've generated for my reverse proxy, I can see it's got enabled TLS 1.0, 1.1 and 1.2. To me, that seems perfectly acceptable. SSL 2.0 and 3.0 are insecure and rightfully disabled.
I'm not sure if TLS versus old SSL is the problem here, but I thought I'd mention it.
I'm just hoping we can get this fixed either way.
I'm running GUI 5.0.1 on Windows 10, against Transmission 2.92 in this docker on unRAID OS. The reverse proxy runs in Apache 2.4.18 on Ubuntu 16.04.2 with kernel 4.4.0-64. Let's Encrypt certificate was installed using their automated tool - I don't really know enough about certificates to give any meaningful details.
Turns out it's trying port 80... on a HTTPS connection. Well done.