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I take pictures of fox hunting, and the hunters wear helmets that cover their foreheads. I try to put the hairline and forehead where I think it ought to go, but has anyone faced this problem before? Solutions?

If the light is from the front or side, then I get deep shadows under the eyes. Backlit with dodging of the face works best, but I pray for cloudy bright days.

I use Aperture 3.1.1 with Portrait Professional as an add on.
If the hairline is hidden, then either just leave it where the software places it, or put it where the hairline would be if it could be seen.

For improving a portrait's lighting, have you tried playing with the skin relighting sliders, especially the one called relight, it can remove hat shadows and that kind of thing.