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This may sound like a strange problem, but has anyone not been able to get the dipstick back into the tube? I changed the head gaskets on my '85 recently and to get the stock exhaust manifolds in and out, I removed the dipstick but left the tube attached to the engine. After putting the exhaust manifolds back on, the dipstick would only go in about a foot. I tried putting different bends and twists in the dipstick, and even narrowing the tip of it, but its still a no go.
I am able to pass a thin piece of wire down into the pan through the tube. The tube itself is stuck into the pan tightly. I don't think I can remove the tube without breaking it or having to drop the oil pan.
Put headers on last year and mine was broken about 3 inches from the end of the hole. I had to pull the pan in order to remove what was left of the dipstick tube. It was like the end of the tube has a shank or something in it and easy removal just isn't in the cards. I beleive you are going to have to pull the pan.
I thought that at first but I inspected the tube and there are no kinks in it. It lines up with the hold down near the starter and the tang that hooks on an exhaust manifold stud.
Yes, I tried oiling the dipstick. It didn't seem to help.
The dipstick has always been difficult to get in and out of the tube since I bought the car in '97.
I can pass a thin wire through the dipstick tube but I needed to put a little bend in it right at the tip. It feels like there is a lip or something partially obstructing the end of the tube. I don't know what it could be, unless it's just the angle at which the tube enters the pan.