This was happening to me too. I was told from some guys on here that it could be a bent shifter fork or worn gears (from jamming into gear).
If you force the shifter, this can bend the shifter fork. When I serviced my rearend I found the shifter fork bolt was a little loose. I tightened it up, and haven't had any trouble since. Good luck!
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1966__122 Cub Cadet.
Owner: Calvin, 6 yrs old
Dad: Craig
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