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There is a valve on the transmission that controls the high low. It is most likely filled with gunk and needs to be cleaned and/or replaced. They get moisture in them and oil which causes the o-rings in it to bypass the air internally and it doesn't slide the piston as it needs to and yo get the exact issue you have.
Have that valve checked. If you do it, it is on the top, back of the transmission. You will see the air lines going to it from the gear shifter. Don't mix the lines up.
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