Hi,
I've just tested Orthanc with the attached configuration files and a self-signed certificate. Started it with this command:
C:\Program Files\Orthanc Server>Orthanc.exe --verbose C:\Users\Alain\Downloads\test-tls-orthanc\orthanc.json
Note that, at that time, my Orthanc running as a Windows Service is stopped -> it works fine.
If my Orthanc Service is running, I get an error stating that the TCP port is already in use (which is expected).
You may also try with another "HttpPort" in your configuration file to check if it helps or not...
HTH,
Alain.