Additionally, what versions are you attempting to use? The Designer Launcher in 8.1.7 now goes directly to /StatusPing for checking the connection where it previously hit /main/StatusPing and the redirect from the gateway tried to redirect to HTTP and was thusly rejected due to downgrade. See this thread for reference: Hard coded request for HTTP in Designer Launcher even if gateway set up for HTTPS - #11 by kcollins1
The feature @jspecht references will definitely help smooth the experience out and address some of the other issues (related to client IP reporting).