One problem related to transmission stuck in gear has been reported for the 1999 Jeep Grand Cherokee. The most recently reported issues are listed below.
While driving to work the transmission got stuck in first gear and would not shift into second gear or anyother gear for that matter. I was stuck driving a maximum of 20 mph to work. I had to get the vehicle towed to the dealership. Since then I have had problems with the transmission shift hard between first and second grear. (dealer has tried making adjustments which do not seem to help). I also have noticed that when shifting into reverse a loud whinning noise can be heard from the transmission. The dealer says this is normal. The reason for this is the transmission is filling up with fluid. I find this explanation unacceptable I have never heard a noise like this from my 1993 Grand Cherokee or anyother car for that matter. I have read hundreds of reports of unsatisfied 1999 Grand Cherokee owners with transmission problems, and I think Chrysler needs to do something about it. I have asked Jeep to replace my entire transmission several times, but they refused.