A heel insert is provided for an article of footwear that includes an upper defining a foot-receiving cavity having an ankle opening. The heel insert includes a base. The heel insert includes a spine extending outward from the base to a tip of the spine such that the spine extends upward along a posterior wall of a heel region of the upper toward the ankle opening when the base is operatively connected to the heel region. The tip of the spine is moveable relative to the base between a first position and a second position along a longitudinal axis of the article of footwear. The heel insert includes a spring operatively connected to the spine such that the spring biases the tip of the spine toward the first position of the tip. The tip of the spine is resiliently deflectable toward the second position against the bias of the spring.