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if memory serves me correctly, Jeep pulled the manual transmission on the Grand Cherokee in 1999. so this means you are dealing with an automatic. Now whether or not your JeeP is equipped with "shift on the fly" four-wheel-drive, or a Quadra-Drive II system, i would not know. and seeing as how i do not know much about Quadra-Drive II systems, i will assume you have a shift on the fly model (which is most popular anyway). whenever you are towing a four-wheel-drive vehicle with automatic transmission, you will put the transfer case (the little lever that allows you to engage the four-wheel-drive) into N (neutral) and leave your vehicle's transmission in P (park). this will disengage your transmission and allow the wheels to spin freely without harming your gears. as always, it is best to consult your owner's manual. and if you have Quadra-Drive II.... i am sorry Eric T. Beaver

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