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Had a similar problem in mine. When I applied brakes while head lights were on, the the light would go off completely. There is a computer chip in the tail light assembly that tends to go bad causing the light to malfunction. I just bought a new tail light assembly from eBay and now it works perfectly. As easy as putting in a new bulb but you just have to unplug electric terminal from the light and plug in new light once received.
There is 2 screws located on the side when you open your tail gate by the tail light. remove these 2 screws and pull the tail light out and disconnect the wire connector. Hope this helps.
The 1999-2004 Grand Cherokees had some lighting issues with the tail lights. First check to see if you have power back there with a test light, if you do try changing the bulbs. If that doesn't work, Inspect the bulb sockets to see if they are burned. The issue that I saw the most was the tail light housing being warpped and breaking contact with the bulb socket. The only fix to that is to replace the tail light assemblies. Hope this helps.
open the lift gate. look on the side that you are taking off. there should be two phillips head screws holding on a small bracket. remove them. next gently pull on the tail light assembly. once loose unplug the wiring harness and you are done. installation is reverse of removal.
Look inside the portal where the lamp is installed for a trace of chaffing of the Insulation of the Light harness, or a rough spot over the length of which that one light harness travels. The fact it is intermittent would indicate a minor "FIND IT" problem. Sometimes a Ball acher, but persevere. Better still, acquire a Circuit Tester with "Ohms"on the Scale. Take out the bulb, and connect the RED wire of the meter to the Bulb power terminal and the BLACK wire to a Vehicle clean steel body area, as a Grounding point. If the meter "BEEPS" that indicates a Ground out/Short in that circuit, which is proof positive of a chaffed wire in the harness.
Best of luck in your endevours.
Regards,DT
This type of problem can be caused by bad ground connections. Find as many as you can and clean the surfaces between the loop the screw goes through and the chassis (body). Take the tail light assemblies out and find the ground wires - black wires screwed to the body. Look under the hood, Pull the headlight assemblies out if necessary and find those little guys. They are generally close to the light. Follow the wire loom back from the lights and look for the black wires coming out. Loosen the screws and work the loop back and forth against the metal. Sometimes there is paint on the metal and the screw is the only thing making the connection. Work the screw in and out snug it against the loop and rotate the loop to freshen the connection.
I have taken my car to many shops to solve this problem. Long story short your tail light has a bad circut and entire lamp must be replaced. (Lamp cost approximate $130.00)
Check the relays associated with the tail lights, I believe that the tail light relay and the turn signal relay are two different entities. Hopefully that helps.
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