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Try enabling some of the disabled-by-default options on the Debugger > Introspection page. I'd try one at a time since these can cause problems because they execute actual Python code to get values. You'll need to restart debugging for the option changes to take effect.

A lot of Python debuggers do that by default but Wing doesn't because we prefer to avoid crashing or hanging up when there's buggy code involved. Also, in Wing you can always use the Debug Console to inspect values you're interested in if they aren't complete in the Stack Data tool.

Please let me know if that doesn't help.