Can Netcat talk to an encrypted port?
Solution 1:
You should use openssl s_client -connect server:port to debug applications over SSL connections.
Solution 2:
You probably want to make use of the openssl s_client -connect command.
However it looks like this doesn't accept piped input as you might use with netcat.
If the application is just an HTTP server then you can use standard terminal entry to perform your session.