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if you have overdrive in that car it means that your about to go into overdrive
what would transmission not to shift in to overdrive
the overdrive sencer
If your 1997 Chevy diesel will not shift into overdrive, you might have an issue with a transmission sensor. Some of these vehicles have several sensors that must engage in order to shift.
If the overdrive switch is turned off then the car will not go into overdrive. As it is not in overdrive, then it will not downshift out of overdrive as it normally would. It also will not shift to 3rd gear above a certain factory preset speed. Turn th overdrive on and see if it operates normally.
Linkage adjust
dirty trans fluid might be the cause. have it changed, but not flushd
it has a malfuction so its setting a code
something is wrong in the transmission. It will have to be diagnosed. You probably have a bad shift solenoid in the tranny.
you push the button at the end of the gearshift to engage it, its for towing vehicles or carrying a good size load I think you have it backwards. It is by default in overdrive. Pushing the button on the end of the gear selector will disable overdrive. You would want to disable it to pull heavy loads or if you are in a hilly area, especially at lower speeds.
a long term cause
A malfunction has been detected - get it checked out