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Troubleshooting
Do "Web Inspector>Show File Mapping". Do you see a successful mapping between the source file and the URL? If not, make sure you have opened a sublime project, or folder. Mappings are created by matching paths returned by "sublime.active_window().folders()" against paths returned by the browser. The easiest way to fix this is to do "File>Open Folder" in Sublime, and then opening the source file from that view. Then start debugging and toggle the breakpoint.
Symptom is that after doing Web Inspector>Start Chrome (and Chrome launches) you then do Web INspector and see Start Chrome, not Start debugging. The most common cause is that an instance of Chrome was already open, so the port 9222 was not respected. Close instances of Chrome and try again. Also try adding "chrome_profile": "other" into your Web Inspector settings JSON file.