I've run into an instance where I created a new query window, right-clicked to connect to a server and found the following options:
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Come to find out the reason this happened was because I created the new query window from a multi-instanced registered server such as below:
Just make sure to create your new query window from a single instanced registered server.

John Waclawski
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Sadly, I have this problem with SSMS 18, but we have no registered servers at all, so that isn't the problem. In my case, if I leave SSMS open overnight, with connected windows, those windows will all be disconnected by the morning, and all connection options disabled. The only solution is to open a new query window, which works fine (until left connected overnight). This is quite annoying, since I might have 5 or 6 such open windows. Even if the server is set to disconnect after an inactive period, SSMS shouldn't then block any subsequent connection the user might want to make (or reconnect). – RBerman Oct 02 '19 at 15:08