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There is some added logging that can be turned on and off for different sub-systems with the internal-*-logging-start/stop commands, and this goes into the ide.log file in the user settings directory. You can see the logging commands by doing Edit > Command by Name and then typing 'internal'. The available commands are shown in the completer.

They are also listed in https://wingware.com/doc/commands/toplevel (search for 'internal-').

However, this is probably best done on request of Wingware support staff, since the output may be difficult to interpret and/or not relevant to the problem at hand.

You can actually also get the source code under NDA and debug Wing with itself. But things like the analysis system are hugely complex asynchronous code so it may not be that much fun to try to track things down on your own. :-)