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In gripping devices, adapting to highly unstructured environments such as irregularly shaped objects and surfaces continues to be challenging. To achieve safe and reliable gripping, many researchers have employed various underactuated mechanisms such as differential and compliant mechanisms. All these mechanisms have demonstrated successful gripping performances. They, however, have hardly considered scalability issues of underactuated mechanisms originating from additional force transmissions and onerous mechanism assembly. In this paper, we propose a structurally simple and scalable underactuated mechanism. The mechanism is demonstrated on a gripping device called the “Buckling gripper.” The Buckling gripper achieves adaptive gripping on rugged, uneven, and undulating surfaces typically found in the natural world. The key design principle of the Buckling gripper is inspired by a caterpillar's proleg that highly deforms depending on the shape of the contact surface. This key principle is applied to the gripper via flexural buckling. Normally, buckling is avoided in mechanical designs, but the buckling behavior of a flexure with an adequately selected length provides wide gripping range with a narrow range of force variation, which provides a sufficient number of contacts with even contact forces. As a result, the Buckling gripper achieves adaptive gripping on various surfaces, similar to a caterpillar.