If your shifting mechanism is all in good condition and this still comes out of gear probably the teeth on the gears involved are worn from grinding into gear. The teeth get chipped/worn so they have a small angle to them that, when power is applied, causes them to slide apart. I haven't seen this in a Cub specifically but in other transmissions. If it isn't a transmission with sliding gears then the "dog" teeth that engage get worn the same way from grinding and cause the same problem. If the shifting fork and shifting mechanism has to hold the gear in position under load it will wear out the shifting forks as they are not designed to hold gears under end thrust, just to move them. When in position they should not be moved by the power flowing through them which worn teeth can cause to happen. This wear can be very slight and difficult to see. It can look like a taper on the tooth from one end to the other. Or on "dogs" the engagement surface will be rounded off and then slightly tapered. Both cause end thrust to the gears which cause them to move and overcome the slight resistance of the shifting mechanism and them "pop" out of gear. You do want to make sure the shifter is working right and shifting it all the way into gear.
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Today's Featured Article - Hydraulics - Cylinder Anatomy - by Curtis von Fange. Let’s make one more addition to our series on hydraulics. I’ve noticed a few questions in the comment section that could pertain to hydraulic cylinders so I thought we could take a short look at this real workhorse of the circuit. Cylinders are the reason for the hydraulic circuit. They take the fluid power delivered from the pump and magically change it into mechanical power. There are many types of cylinders that one might run across on a farm scenario. Each one could take a chapter in
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