fwiw .. I found ...
swing the leg as you grease it, it helps to get it through. Also you'll have previously regularly done the steering head as well, accessed in engine room at top of transom internally - swing steering as well. Presume your on water type aqua grease ??
Found on mine that after a few years of non greasing by 'engineers' (ta vp agent) the grease inside the steering head went solid and plugged up the journels that carry the grease down into the moving bits causing wear to bushes and eventually the dribble of water internally ...