The present technology relates to an imaging system, a warning generation device and method, an imaging device and method, and a program capable of more simply checking an imaging situation.A camera-control detection processing unit of the imaging device performs a detection process for various types of control based on a captured image, and an image quality control processing unit detects occurrence of abnormality corresponding to each cause based on the result of the detection process. A warning determination processing unit generates a warning flag indicating whether or not abnormality occurs based on the detection result by the image quality control processing unit, and a wireless transmission unit transmits the warning flag to a warning generation device. A wireless reception unit of the warning generation device receives the warning flag, and a warning means control processing unit instructs warning according to the warning flag. A display processing unit displays a warning icon on a display unit according to the instruction of the warning means control processing unit. The present technology can be applied to an action camera.