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THE TRANSMISSION IN THE MODEL IS ELECTRONICALLY CONTROLLED SO WHEN A PROBLEM LIKE THIS OCURRS IT IS IMPORTANT THAT YOU HAVE THE COMPUTER CONTROL UNIT SCANNED FOR FAULT CODES. I THINK IN YOUR CASE YOU WILL NEED TO REPLACE A PART CALLED THE "VEHICLE SPEED SENSOR", IT SENDS A SIGNAL TO THE COMPUTER TO INDICATE WHEN OVERDRIVE CAN BE ENGAGED, THIS IS ABOUT 35 MILES PER HOUR IN MOST MODELS.
The overdrive solenoid is connected to the transmission itself on this Volvo. You will find the switch on the passenger side of the transmission. It looks like this
As a means of testing operation of the solenoid - you can ground out this switch by turning the key in the ignition into the on position. Make sure engine is off and the transmission in 4th gear and listen for the click of the soleniod on the back of the overdrive. Also the light on the dash should iluminate as well.
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There isn't anything wrong with your car. This is perfectly normal. I have a 2000 ES300 as well as other people that I know and it operates in the same way. Overdrive doesn't mean the same thing for every car or transmission. In our case overdrive is simply a reference to the top gear which is 4th gear. When you switch overdrive off(which is depressing the button causing the O/D OFF dash light to illuminate,) the highest gear becomes 3rd because you turned 4th gear or overdrive off. The application scenario for this is usually mountainous terrain where a lot of uphill driving makes it more feasible not to up shift into 4th gear while ascending and descending. It will not switch back to overdrive or 4th gear until you re-engage it by turning the overdrive back on or repressing the button. Again, when the O/D OFF dash light is illuminated, overdrive which is 4th gear is off and the highest gear will then become 3rd. It will never shift into 4th gear while this light is illuminated or overdrive is off. When you press the button and the O/D OFF dash light is NOT illuminated overdrive is on and therefore it will shift into 4th gear as usual. This applies to all 97-2001 ES300's and probably any other car you drive tat exhibits this same type of change when overdrive is turned off.