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An oil dipstick may not go completely into its sleeve if it is bent or damaged. It may be designed to only go in one way try turning it 180 degrees and putting it in. Also, if it is not the original dipstick it may be the incorrect size or too long.
Other possibilities that come to mind include: a damaged sleeve, foreign material in the sleeve, or part of the oil dipstick has broken off in the sleeve.
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