Is there a rod, right in the middle of the receptacle where the winch handle engages? There should be, and you should have to push the rod down, when you insert the handle. The rod disengages the electric motor
It can be stuck, making it difficult to insert the handle, or if under load from electric use, it will prevent you from inserting the handle. You should be able to push it down with a strong finger, is it is working smoothly. But getting the handle engaged is not what you described.
The rod just slides out, maybe is was lost
or never inserted. Is this a new boat
? I got a new boat
and I have struggled a bit with the handle issue. But not as you describe. I have removed the rod and considered a racing
rod, that disables the electric motor
, that cannot be your problem.
Good luck getting to the bottom of this.