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I don't have a winch truck but I don't see why the same process can't be used. Worst case the excess grease seeps out of the seal. I don't know how much it would hold though.
The steering box holds 3 1/2 tubes of grease. I forget the size bushing I used, but I screwed a zerk fitting into a brass bushing. I then screwed that into the bottom drain hole. Then pumped until grease came out of the fill hole.
Not exactly uncommon for a steering box to leak. You basically have 2 choices. Either rebuild the steering box or fill it with John deere cornhead grease.
Obviously the correct way is to rebuild the box. Though it isn't an uncommon thing to fill a manual steering box with flowable grease...
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