"There is a clutch dog with te
"There is a clutch dog with teeth that match teeth in the gears. When you shift, these mesh together for the ride. When they have been slowly shifted so they rattle in gear, or just from use, the teeth get rounded and won't hold.
OR; the shift cable is mal-adjusted or some of the nylon bushings in the system are worn. Try to disconnect the shift cable and see if it will shift further into gear than it does with the control box. If so you may have a universal control box that should be adjusted internally for more "throw" in the movement of the cable.
See if the adjustment of the cable is right in the middle of the shifter when in neutral.
You may have an early single piece small lower unit. These required special tools and guages to rebuild."