In May 2004, he completed the first free ascent (FFA) of Dihedral Wall. In 2005, he and Beth Rodden—swapping leads—made the third and fourth free ascents of The Nose. Two days later, on October 16, Caldwell free-climbed The Nose in less than 12 hours. A few days later, Caldwell climbed The Nose in 11 hours, descended the East Ledges, and then climbed Freerider, topping out 12 hours later – the first ascent of two El Capitan free climbs in 24 hours. On El Capitan, Caldwell has also free-climbed: Lurking Fear, Muir Wall, West Buttress, Salathé, Zodiac, Magic Mushroom, The Dawn Wall, and New Dawn.