One problem related to transmission fluid leaking has been reported for the 1999 Jeep Grand Cherokee. The most recently reported issues are listed below.
I own a 1999 Jeep Grand Cherokee and since the purchase date I have had problems ranging from brakes to check engine lights, most recently the transmission is beginning to leak fluid. I have contacted Jeep and the local dealer about this issue and they are not willing to step forward on this issue. The vehicle has 30,k miles and is a 3rd vehicle for me to use, so it does not get a lot of usuage. At this point I would consider this a complaint issue as the vehicle is in immaculate condition, except for the leaking transmission. I would like to inquire as to the number of '99 Jeeps that are experiencing the same issue. I have been communicating with other Jeep owners that have the exact same issue. I have encouraged them to do the same as I am with my filed complaint. Also, Jeep has been extremely arrogant about their responses to "not assist" with this matter.