And why is the "Select server automatically" box still checked?

You seem to be using the same server as in the previous screenshot. I just tried it and my Electrum doesn't synchronize with it (btc.smsys.me with port 995).

Uncheck "Select server automatically", right-click a different server, "Use Server", click "Close"; That's it. Keep the checkbox unchecked.

Try selecting the server electrumx.ddns.net - I just tried and it synchronizes (as of now).