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This means the debug program crashed, was killed, or our debugger encountered some serious internal error.  The "debug server" is the part of the debugger than runs inside/with your code, not a separate process.  To diagnose what is going wrong, set the Debugger > Diagnostics > Debug Internals Log File preference in Wing and replicate theproblem.  You can email the output to if the cause isn't obvious from looking at it (which it likely won't be ;-).