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Q: The bolt on the chain guide is loose.

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if the top bolt on a fixed chain guide falls out would it fall into the oil pan?

If the bolt is loose and is able to work it’s way out and there is room for the fall, then yes it may fall into the oil pan. If the engine is running when the bolt decides to fall, it may get caught up in the moving timing components and may not be pretty if it causes damage. Consider hiring the assistance of an experienced technician who is willing to come out and take a closer look for a more personal diagnosis.

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