Almost every action in winIDEA can be scripted using winIDEA SDK. 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 Debug | Breakpoints.
3. Enable Script in the Action section and select your script. When the application stops at the selected breakpoint winIDEA will execute the script.
For a more detailed visualization follow the Breakpoints Tutorial.