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The server disconnects from the host regularly. MTVS should be smart enough to pair with the same machine again before prompting me with the pick a server. Maybe allow setting a preferred machine that it will auto pair with if it sees it and never prompt the pairing window.
Verified this bug with Xamarin.iOS for VS 1.6.60.msi. If Xamarin.iOS for VS disconnects from build host, it recognises the previous paired host machine again, unless it was unpaired before disconnecting. However for this to work, user still has to select the same build host from "connect to a server Xamari.iOS build host " list and click connect button.
I think the issue reported is fixed, since no pairing window is shown.