When you reach the OD cut-in speed, usually 27 to 30 mph, listen for a snap from underneath the car indicating the solenoid is energized. When you lift off the gas it should complete the shift, you will feel a slight lurch as the shift completes. If it freewheels when you let off the gas above the cut-in speed it is not going into OD. It's usually an electrical problem between the governor and solenoid, or the solenoid itself. You can test the solenoid by connecting a long wire from the battery to the solenoid terminal on the relay. When you touch the wire to the terminal you should hear the solenoid click. If it doesn't the wire from the relay to the solenoid is open or the solenoid is toast. Also check that the OD shift lever has full travel in both directions when you push/pull the cable.