I seem to recall that happening to me awhile back. I asked the Wing
guys to help and they suggested using this code to connect:

"
import wingdbstub
if wingdbstub.debugger != None:
        wingdbstub.debugger.StartDebug(autoquit=False);
        print 'Connected to wingIDE'
else: print 'Could NOT connect to wingIDE'
"

which keeps a persistent connection.

Is that how you're connecting to Wing? You see the Bug in lower left
turn Green, I presume; at what point does it switch back to white?

-jason

-- 
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