Are you talking about the dipstick itself or the tube? My dipstick has been lose for years, bought a replacement O ring once but almost couldn't remove the dipstick. Stuck the old one on and gave up.

Now the tube itself should seat pretty solid. Wrong O ring maybe?

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2016 Corvette Stingray 2LT
1969 280SE
2023 Ram 1500
2007 Tiara 3200