If I turn the engine off while going down the road and turn it back on it shifts fine. It seems to do it more when its raining or there is alot of moisture in the air.
My 1994 Caravan sometimes does not want to change gears. on 1994 Dodge Caravan
it is going into limp mode. you need to have someone find out why this is happening. turning it off resets the system and works till the fault happens again. get it checked asap before damaging the trans.
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Have ignition switch checked for intermittent failure. Maybe check with local dodge dealers parts dept. , they may confirm that , and if they stock the switch that's almost a definite 'yes'.