This is the reason I am replacing the engagement arm. It would be an easy fix but the part was cheap.I've been following this just out of interest. Looks like Kubota did away with the overrunning clutch on the new parts. I don't see the need for it with HST - you can still control the tractor speed with the treadle.
By the lack of wear on the lower part of the coupling ramps, I'd say the old one wasn't fully engaging. Probably good you replaced the engagement arm.
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