Almost every action in winIDEA can be scripted using isystem.connect API. Combining the scripting feature with the ability to trigger such scripts you get a really powerful combination that can be used for all sorts of things.
1. Create an initialization script via the Watch Window and save it to your PC.
2. Open the Execution Breakpoints dialog.
3. Enable Script in the Action section and select your script. Each time the application stops at the selected breakpoint winIDEA will execute the script.
For a more detailed visualization follow the Breakpoints Tutorial.
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