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I had a leak about 10 yrs ago from the dipstick and just replaced the o-ring.
Short story long....
I did a lot of searching and found that after removing the tube, I could grab the part that attaches to the oil pan by the portion that the tube attaches to with a small pair of needle nose vise grips, one side in the tube and the other on the outside. Just don't crimp down on it like the hulk and it holds it easily. I then loosened the nut, and it slid over the small vice grips. That gave me room to finagle the old o-ring out over the pliers as well. The pliers don't let the part fall in so I was able to clean up the inside surface enough for a clean seal Then I put a small dab of bearing grease on a couple of spots on the flange with the groove and fed the new o-ring over the pliers and in to place. The grease held the new ring in the groove. Fed the nut over the pliers and tightened it down. Hasn't leaked since.
In the 19 years I had my truck, I was fortunate enough to never have to deal with this leak potential. In fact, I guaranteed that I would never have to deal with it by having a weld-on dipstick housing installed when I had to get the motor pulled for something else (slightly warped timing cover that would not seal up). Granted, I think there are either one or two small diameter o-rings on the dipstick tube itself (where it push fits into the housing), but any leak there would be nothing in comparison to the potential drama of the housing o-ring leak.
Put a few miles on it running down a bad road or two and over some bouncy railroad tracks. Crawled under it today to see it's all good and still dry. Planning on taking it on a road trip down to south Texas to spend Christmas with our oldest daughter and son-in-law. If everything is still holding up afterwards, I'll plan on doing the F350 too...
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