This is difficult to summarize, but here goes nothing. I would assume I'm missing some fundamental expectation, except that I'm sure I've seen this "just work" in the past...? Repro: 1. Launch Safari (see notes). 2. From the Develop menu, set "Automatically Show Web Inspector for JSContexts" (for convenience). Don't set "Automatically Pause Connecting to JSContexts" yet. 3. Run `run-jsc --remote-debug`. REPL or long-running script doesn't seem to matter; I'll just assume the former here. 4. Web Inspector appears automatically; attempt to click pause on Sources or record on Timelines. A. Nothing happens! \(^o^)/ Whatever you clicked turned to a grey state, but otherwise WI just sits there (even as you continue to do stuff on the REPL). 5. Kill JSC, set "Automatically Pause Connecting to JSContexts", re-run JSC. 6. Web Inspector appears automatically; hit record if you'd like a timeline, then type something into the REPL. B. Auto-break! We can step-debug and use the console freely for one glorious moment. Even timelines sort of works if you hit record before. 7. Eventually, hit the play button, then return to step 4 / outcome A. Notes: Ideally we'd use `run-safari` but that greys out the Develop menu, so I used latest STP. (Even more ideally would be `run-minibrowser`, but to my knowledge that doesn't allow for JSContext inspection.)