Plantar fasciitis is a common injury to the plantar aponeurosis, manifesting as pain surrounding its proximal insertion at the medial calcaneal tubercle. Pain is typically worse in the morning when getting out of bed, and may subside after the tissue is sufficiently warmed up. For running-based athletes and individuals who spend prolonged periods of time on their feet at work, plantar fasciitis may become recalcitrant to conservative treatments such as ice, rest, and anti-inflammatory medication. Exercise-based therapies have received only limited attention in the literature for this common problem, yet they are becoming increasingly validated for pain relief and positive tissue remodeling at other sites of similar soft-tissue overuse injury. This study reports on pain outcomes in individuals experiencing chronic plantar fasciitis whiles wearing a shoe with an ultraflexible midsole (Nike Free 5.0) (FREE) versus a conventional training (CON) shoe in a 12-week multielement exercise regimen, and after a 6-month follow-up. Adults with = 6-month history of painful heel pain were recruited and randomly assigned to wear 1 of the 2 shoes. All subjects completed the same exercise protocol. A visual analogue scale item tracked peak pain in the preceding 24 hours taken at baseline, 6- and 12-week points, and at the 6-month follow-up. Twenty-one subjects completed the program (9 FREE; 12 CON). Both groups reported significant improvements in pain by the 6-month follow-up, and the FREE group reported an overall reduced level of pain throughout the study as a result of lower mean pain scores at the midpoint and post-test compared with the CON group. The exercise regimen employed in this study appears to reduce pain associated with chronic plantar fasciitis, and in doing so, the Nike 5.0 shoe may result in reductions in pain earlier than conventional running shoes.