Climbing robots have many potential applications including maintenance, monitoring, search and rescue, and self-assembly. While numerous climbing designs have been investigated, most are limited to stiff components. Flippy (Fig. 1) is a small, flipping biped robot with a soft, flexible body and on-board power and control. Due to its built-in compliance, flipping gait, and corkscrew gripper, it can autonomously climb up and down surfaces held at any angle relative to gravity and transition from one surface to another, without complex sensing or control. In this paper, we demonstrate the robot’s ability to flip consistently over a flat Velcro surface and 2D Velcro track, where it reliably climbs vertically, upside down and back to a flat surface, completing all the interior transitions in-between.