Problems With a Jeep Cherokee Transmission
Although they are pretty stout units, even the transmission in a Jeep Cherokee can experience issues. Some of the symptoms are soft shifting, not shifting and slipping in and out of gear.
The first thing to check if your Jeep Cherokee isn't shifting correctly is the transmission fluid level. It is the yellow dipstick located on the passenger side of the engine, back by the firewall.
If your Jeep Cherokee regularly tows or otherwise carries big, heavy loads, the transmission's bands could be slowly burning up. An aftermarket transmission cooler will save the day in that scenario.
If it is difficult to get the Jeep Cherokee in and out of gear, it could be a linkage problem. You can check it out by removing the panel with the gear indicators on it and then moving the shifter. Look for binding or other issues.