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If it's an automatic, probably an electrical fault in that circuit. If it's a manual , more than likely bent clutching teeth on the 4th/5th synchronizer. I have an 89 auto that had a symilar problem. It was a blown thermostat. EXACTLY. If the vehiicle does not reach a certain temperature the trans. wont shift into overdrive. I had this problem years ago and it took 3 genius dealers to figure it out!!!

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Q: Why would a 1989 2.6 Trooper auto not go into overdrive when it should?
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