I’ll have a look at the old fittings and see what I can see.

 

I cant remember whether there is one or two o-rings in there

its possible to leave an old one in there, or damage the new one/s

its hard to see in there, I fished one out with dentist pick tool

you can buy new o-rings (and the 3/8" 10mm plastic "fuel injector fitting"

or replace the entire fitting with a screw in adaptor with 3/8" barb, and rubber hydraulic hose all the way, no steel...(although no doubt you dont want to do this)

I did this cause RHD lines are hard to get and/or expensive, and I didnt like that poxy plastic disconnect

 

Looking at the old fitting there is one o-ring on the male portion and one on the female side behind the plastic clip. I think what happened is the tension from the new, poor fitting, lines damaged the female side o-ring. I can remove the fitting and warranty it but it will likely happen again so I guess I need to try and bend the line.
I could buy the fittings with a barn and do rubber lines but they are expensive and I’d be wasting a lot of money I just spent on the factory fittings and new lines.

 

looking at your second pic, there appears to be 2 O-rings inside ?

they are green in color

 

Correct. I found one of my old fittings. Two o-rings. Green. They are 1/16" thick with an OD of 1/2". ID looks to be just shy of 3/8".

 

I removed the fitting today and warrantied it. A couple of weird things I found, the fitting was not very tight (I definitely tightened it when I installed it), the male threads o-ring was in pretty bad shape but it didn't look to be leaking from the threads just the female quick connect even though that o-ring looked okay.
1. Does anyone have the torque spec for the fittings? I couldn't find it in the FSM
2. Should I replace the Dorman male thread o-ring with a nitrile o-ring from my HF assortment (if I have the right size) since the last one got destroyed when I tightened it? - I lubricated all o-rings before installing them -

 

Still dealing with this...
I do not have time to touch or drive the Jeep very often, today I did. I planned on driving the Jeep if the new fitting(s) weren't leaking, so I took a peak under, and sure enough, there's a drip on the fitting. Not sure where to go from here, I'm tired of it being undrivable due to a $12 fitting. The first time it leaked I spent a while bending the lines to have less tension on the fittings and thought that would do the trick, nope. I can think of a couple solutions each with a downside.
1) Replace the fitting again, this time replacing the o-ring. Downside: Draining all the fluid yet again
2) Try reinstalling the factory fitting since they weren't leaking. Downside: Draining all the fluid yet again and reusing old o-rings
3) Spend the extra to buy the barb fitting. Downside: Draining all the fluid yet again and not sure if the lines would need to be flared or if a hose clamp would be sufficient.

 

I ran a clamp and regular ol' hose out to an aftermarket cooler coming off the other end of that tube without issue for a few years. As long as the clamp was good and tight, the hose didn't move. There's not much pressure on the cooler circuit, around 60 psi if I'm not mistaken.

I will say that replacing the whole kit-and-kabootle with AN fittings and regular ol' hose is pure heaven. Break the AN hose end loose with a wrench and it can be removed the rest of the way with just your fingers. Similarly, if you align the hoses well when you install it, it all falls right back into place and threads on easy as pie. I'm pretty sure I have less than $100 into it using mostly Summit barbed AN fittings and regular ol' transmission cooler hose. No clamps are needed; looks really clean... Not what you asked for, but ...

 

Conversion to AN lines is a winner! I modded the stock Trans fittings, an-6 male out on each, no adapter fittings. ( machinist by trade, simple mod). Stainless hard lines, braided hose collects mud.

Fittings method for an6 swap

The machinist way to get there. 😝

 

What thread size is needed for the trans to convert to AN? I'd be probably going with -6 braided line since I have a ton of it or if I get lazy just run a barb with hose.

 

Transmission: M14 x 1.5mm w/ O-Ring (Not sure what I ordered...)
Lower Radiator Fitting: https://www.summitracing.com/parts/EAR-751166ERL
Upper Radiator Fitting: https://www.summitracing.com/parts/SUM-220667B
90° Hose End for rear transmission and upper radiator connections
45° Hose End for front transmission connection
Straight Hose End for lower radiator connection (and a bit of clearancing w/ a ball peen hammer)