If your connection doesnt work with first time connection to Tor , Whonixcheck will stay into that position of no connection at the first time although it doesnt check back when there is a connection if u add/enable bridges.
whonixcheck is a popup which is only valid at the time shown. I don’t think this can change anytime.
Only thing we can do is make whonixcheck obsolete by improving tor-control-panel etc.