A cooking engagement system for a cooktop appliance is provided herein. The cooking engagement system may include a camera assembly, an image monitor, a lighting assembly, and a controller. The camera assembly may be mounted above the cooktop appliance along a vertical direction and directed at a cooktop surface. The image monitor may be mounted above the cooktop appliance and directed away from the cooktop surface. The lighting assembly may be mounted to the casing above the cooktop appliance. The lighting assembly may include a light source directed at the cooktop source to emit a light thereto. The controller may be in operable communication with the camera assembly and the image monitor to initiate an interactive cooking operation.