Cephalopods (e.g., octopus, squid, and cuttlefish) can change their skin colors and patterns for camouflage or communication. Camouflaging cephalopods attempt to  recreate   the  visual  texture of their surrounding environment on their skin, in part by controlling the size of millions of skin pigment cells, called chromatophores .  How does the chromatophore system generate countless  different  texture-matching patterns? Using computer-vision methods to track  > 100,000 chromatophores in behaving cuttlefish  Sepia officinalis , we quantitatively described camouflage behavior at single-cell resolution. We found that the motion of camouflage patterning appears not to be pre-programed. Skin patterns  meander   in a high-dimensional pattern space in search for a good match with the environment. As patterns “move” along these paths, chromatophores are coordinated in  highly- flexible manners. We further identified a series of regions in pattern space, where cuttlefish tend to hold and compare their skin pattern to environment, as they progressively minimize the difference between them. These findings reveal the complexity of the chromatophore control. To understand how the complexity has evolved, we compared  Sepia  with another cephalopod, the bobtail squid  Euprymna berryi , which lacks complex skin patterns. We found a difference in the organization of their chromatophore  brain regions : a somatotopic map of motoneurons is present in  Sepia  but absent in  Euprymna . Together our studies may start to uncover organizing principles in the neural circuits that generate a high-dimensional motor output, and may reveal how such neural circuits changed adaptively during evolution.