Due to muliple breaks and sprains of both ankles, I now have rolling ankles. When I hike, I have to wear braces with plastic or metal up the sides and under the heel. When I jog on pavement, I use the soft lace up brace (like a corset for the foot) I want to get into trail running, but the hard braces don't really feel comfortable for the gait required for running, but the soft braces don't provide enough stability. Anyone have any suggestions?

I'm sorry to hear that. Maybe you shouldn't get involved in trail running if your condition doesn't permit it. Check with your doctor.