The fluid got into the connector from a leaking conductor plate. There is a real good chance that your trans control module is full of fluid also. The .6 trans are bad about wicking fluid up the wiring harness. Whether or not this will cause a problem is questionable. Some will claim that the fluid will short out the control unit, I'm not 100% sold on that idea though.
It would be best to get a genuine MB conductor plate though.

I'm glad you figured out your issue.

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Mercedes Benz Master Tech - Retired

Its not a good idea to use an offbrand conductor plate in the transmission, its only a plastic tray with copper tracks and a couple of hall effect sensors in it. But the OE parts are better materials

The leaking plug is usually from a worn out O ring on the plug socket which is sold separately, its not too expensive either. And always buy a new genuine one. The plug socket has 3 updates till today - the last one sold by MB or dodge is the correct one.

dodge sell that connector socket for 15 or 17 near my place and the plate too for quite a lot lower than the mercedes dealers here.

just ask for a 09 dodge charger transmission plug socket.. the chargers, challengers, jeep cherokee etc have the same transmission as ours. - the parts will come in mercedes packets.

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2012 BMW X5 (Beef + Granite suspension model)

1995 E300D - The original humming machine (consumed by Flood 2017)
2000 E320 - The evolution (consumed by flood 2017)

Im really glad you got it going, I knew you would.
If most people would put the same effort you did on this one there would be way more positive outcomes. Thanks to youtube and other such technologies, remote assistance is just a click away.
As for the conductor plate and the guide sleeve, I think you can get good parts through Transstar industries. Theyre a supplier for rebuild shops and the parts are usually great quality.
Happy motoring....

Final update, just got back from the shop yesterday after a final conductor plate and plug socket swap. While I had the valve body out I sprayed electric contact cleaner to clean out the plug sensor thing and it looked good. By the time I had everything back together and back in the transmission though I noticed more oil on the plug, all while the plug wasn't even touching the transmission. I was already planning to pull the TCM anyway to clean it out, so good thing I did as the entire case was filled with transmission fluid. After I originally changed out the conductor plate and plug housing it must have sealed properly. I believe ATF just wicked back down the wire from the TCM since I hadn't cleaned the TCM out on the first go. That would explain why the outside of the plug housing wasn't leaking like the original oem one had, it was only leaking inside the actual socket. All is well that ends well though. The new plug socket fits a lot more snug and feels much more secure, and the genuine Mercedes conductor plate did look a lot more high quality than the non-genuine one that was in there before. The car is running perfectly! All that is left is fine tuning the transmission fluid levels, it was difficult to get the transmission over 80 degrees in the shop, so I will probably wait to test it cold and go off the cold reading on the dipstick, I have 5L sitting in there for now.

Moral of the story: Make sure to check your TCM whenever you do a conductor plate swap!!! That would have saved me a couple months of heart ache. A friend of mine actually has a 1999 e320 as well and we put his up on the lift just to check (no limp mode problems or anything) and his plug housing was leaking very badly as well. We pulled the TCM, and it too was leaking fluid. It wasn't as bad as mine, my board was completely submerged in fluid, but the bottom 1/4th of his TCM was coated in ATF. So it might be worth checking just as a preventative measure.

Thanks again for all the help, and thanks RPM55 for pointing me towards the TCM!