Is the tube for a dipstick to the trans supposed to have a gasket or o-ring? I've had this annoying leak from it and despite unbolting it and reinserting it, I still leak out a fair amount of fluid. Getting a little frustrated

Yes the tube has a "O" ring on it. Most likely why you have the leakage.

If the O ring is good may have 2 drop the pan clean the hole/tube end w brake kleen & silicone it. I had a pesky one finally got tired of repeated leaking so I bit the bullet & dropped the pan. Gave me an opportunity to ch the gasket/filter/adj bands. Good visual on the O ring & go from there

I recomend droping the pan,clean with brake clean,airdry,new o-ring and use the MOPAR Black ATF/RTV from the dealer.

well worth the 5$ for the ATF/RTV and new o-ring from the dealer.

also a good time to up the pan gasket for the reusable one from the dealer 727-#2464324ac

thanks guys...I will follow your advice scrathin'...

That's some nice dealer advertising

O ring it and throw some silicone on it. Any kind will do. If it leaks after that the tube could have a crack in it.

Is there supposed to be any kind of seal at the top of the tube, or should it be able to vent?

the dip tube should have a rubber stopper under the tube cap with a small metal washer under the rubber plug.

the flat stick is pinched/staked to lock the washer under the rubber plug.

when in place on the stick,it seals the dip tube and the tranz vents thru the vent in the front pump,at the top behind the TC.( this is were most 4x4 fill up with water when deep water crossing)

Do yourself a big favor. Get the MOPAR ATV. It cost less than a tube of silicone. Unless you can get everything spotless, its 50/50 if the silicone will seal. The MOPAR ATV even sealed a leak from the outside. I had one of those plastic plugs they use for the cheap fluid change seeping fluid. Glopped some of the ATV all over it - bone dry for months now.