If i stop the timer and then restart it it starts to spin just fine. The timer is definitely fine.
Your timer should have a built it pause. This does the same thing as you are now manually doing by stopping and then restarting the timer. During that pause the transmission shifts into spin.
If the timer does not pause the motor on it's own so it can shift into spin then your timer is not fine and it needs to be replaced.
I looked up your model number and it uses timer part # 3953321