What is this leak? How do I fix it?

So, tonight, I went exploring in my jeep (near my house) and found a trail I had never seen before. It had been washed out pretty badly (in multiple places) and I tried driving down it. At one point I got my jeep at a pretty steep angle trying to get through the washout and also laid my jeep down on its belly (nearly high centering). I also was a bit mushy with the clutch and I think I burnt it a little (which I usually know better, but I am a little out of practice).

Afterwards, we noticed some oil on the ground just past where this took place and looked under the vehicle to see a lot of dripping oil on the transmission.

Can you all tell me what happened and how do I fix it?

BTW, this is a 2019 4 door with a manual transmission, if that is helpful.
 

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How many miles? looks like the cursed oil filter housing/cooler.

Take a long zip tie or something similar and slide it down along the side of the oil filter housing like a dip stick.

If it's covered in oil when you remove it, it's the oil filter housing/cooler leaking.

The Dorman oil filter housing/cooler is what I would replace it with.

There are cheaper aluminum units on Amazon, but I wouldn't trust them.

It's not a difficult job but time consuming, the JL has some extra stuff in the way that makes it necessary to drain the coolant.

Oil_dip1.jpg
Oil_Dip2.jpg
 
How many miles? looks like the cursed oil filter housing/cooler.

Take a long zip tie or something similar and slide it down along the side of the oil filter housing like a dip stick.

If it's covered in oil when you remove it, it's the oil filter housing/cooler leaking.

The Dorman oil filter housing/cooler is what I would replace it with.

There are cheaper aluminum units on Amazon, but I wouldn't trust them.

It's not a difficult job but time consuming, the JL has some extra stuff in the way that makes it necessary to drain the coolant.

View attachment 425996
View attachment 425997
Yup and yup. What he said ^
 
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