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I had this same issue on a 2000 model. After checking voltages at the rear lamps with no differences between the two sides, I then swapped the two brake light asseblies. The right side was not working when the lights were on and the brakes were applied, it still did not work when plugged into the left side, but my left side still worked when plugged into the right side. So, that left only the brake light assembly to be faulty. I ordered one off of Ebay, and replaced it with no other problems, except the left went out a few months later!! Try swapping the two asseblies and see if you get the same results.

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Q: Why when you apply the brakes with the headlights on would the brake lights go out on a 2001 Jeep Grand Cherokee?
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