“LEAKING” Automatic Transmission Dipstick Tube

I had the same issue, no matter how many "correct" o-rings I tried. I finally went with the race locking dipstick like this one: ATI 726490: Trick Stick Locking Dipstick & Tube Kit Small Block Chrysler TF727 | JEGS

Instead of the single o-ring, it has a large rubber boot that makes a more positive seal.
Thanks I purchased this and I think it fixed the leak. I had to make a bracket for it.