Systems, methods, and computer-readable media are disclosed for concentric suction cup tools with parallel pistons. In one embodiment, an example picking assembly may include a first piston subassembly with a first air cylinder, a first sliding rail that slides relative to the first air cylinder, and a first suction cup. The example picking assembly may include a second piston subassembly comprising a second air cylinder, a second sliding rail that slides relative to the second air cylinder, and a second suction cup, where the first and second piston subassemblies may be configured to independently actuate from a retracted position to an extended position. The example picking assembly may include a first guide plate with a first aperture for the first piston subassembly and a second aperture for the second piston subassembly, a shell that forms a housing for the picking assembly, and an airflow coupler.