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I had the same problem with my 1988 Cutlass. What you should initially do is check the key that you're using. Is it old or worn? If so, it could very well be the key you are using. I suggest that you get a new key made just to be sure. If this isn't the case, then I'm afraid I'm unable to help. Good luck.

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Q: What is wrong if the key will not turn in the ignition of your 1999 Oldsmobile Cutlass?
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