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It might just not have fuel pressure built up by the time you engage the starter. Try turning on the ignition switch for a couple seconds before you engage the starter, see if that helps. Those engines are known for bad fuel pressure regulators, try replacing it Very easy on driver side of intake plenum held on by one clip and a vacuum hose

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Q: Why does it take 2 or 3 tries for your Chevy 2000 Silverado 4.8 to finally start?
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A 2002 Silverado with 113000 miles on it and when you try to start it the vehicle attempts to start then shuts down After three or more tries it will finally start This doesn't happen all the time?

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