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Whenever I run on uneven terrain or up the hill, my ankle gets pretty painful and sore. After that I have to make a few-day pause in order for my ankle to heal. I can’t remember ever injuring it so I really can’t understand why this is happening to me. The only reasonable explanation would be that I’m a bit overweight.

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That theory makes sense! If you’re overweight and if you don’t wear proper running shoes, that can definitely cause pain in your ankle. My first suggestion would be that you determine your foot type by means of wet print test. And there are three possibilities. You can be neutral pronator, overpronator or underpronator. If you have flat feet and don’t wear appropriate running shoes to correct it, it’s only logical that you should have pains in your ankle when on the hill run. Your foot motion maybe should be corrected by the appropriate kind of shoe. So, hill run, which is a very demanding activity, in combination with inappropriate footwear and a few excessive pounds, can cause pains.
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