Just bought a 99 xj yesterday. I noticed this morning there were a couple of drops of coolant on the garage floor. I got up under the Jeep with my flashlight and pinpointed the leak seems to be coming in between the oil pan and the transmission. It seems like a weird place for coolant to be leaking? Maybe it's coming from above? Anybody have any ideas or suggestions?

 

"Rent" a pressure tester from autozone or another store and pressure test the system.

 

Could be coming one of the heater core lines. ...but do what rgr said

 

Yep. Coming from somewhere else. Oil does that, and has everybody screaming, "Rear main seal!"

It's the lowest point on the engine, so fluids wind up there.

 

It's not oil. It's Coolant.

 

He was referring to engine fluids in general, also due to the tilt of engine and blowback while driving.
Coolant leaking from bell housing is usually a leaking welch/freeze plug that is located on rear of engine block. This leak is often more pronounced when jeep sits for two days. When driven every day, the leaking coolant evaporates or gets flung out.

Transmission needs to be dropped to access freeze plug.
To diagnose, should be able to view enough of plug by removing inspection plates and starter, use a good light and a small mirror.
Here is a picture for reference with transmission removed, coolant is behind the middle plug.

 

Of course check the heater hoses, coolant hoses first.

 

Ok so if it happens to be the freeze plug, how much are we talking to drop the tranny and fix? Is it something I have to do? Can I just keep an eye on the coolant level and go from there? Seems like paying to have the tranny dropped to fix a rubber/plastic plug is a lot if I can keep from having to do it. But at the same time, if it's a major issue, I'll take care of it.

 

Its not rubber or plastic it is brass and it may just keep getting worse or get bigger all at once if corrosion is really bad.

 

whatever you do, please don't use "stop leak" or any of that junk that you poor in the radiator. Unless of course you want to also replace your radiator, heater core, water pump, etc in about a year.

 

Yeah I know not to use that stuff. Just not wanting to spend a grand on dropping tranny if I can just add coolant every now and then.

 

First, inspect engine bay hoses with good light. Coolant leak will usually leave a residue. Any splits in hoses may be noticed better if you squeeze them down the length.
If coolant drips from oil pan fill plug, leak is likely in engine bay. If it drips out of bottom of bell housing, then suspect freeze plug..

 

 

This is best pic I can get.

 

Hmmm, looks like rear freeze plug, the way it has a direct trail. It's fresh, if the leak is in hoses it would be obvious.
Problem with continuing to run jeep is the potential for complete failure of plug. Plug is around 2" diameter.. Replace with brass.

I did mine myself, home garage, took two full days. But now having done it I could do it again in one. Will need a transmission jack and E-12 socket.
Maybe read up on the process and watch you-tube video of it. Then decide if it is something you wish to tackle.