It is an object of the present invention to provide a driving support information generation device, a driving support information generation method, a driving support device, and a driving support method which make it possible to present effective caution information to drivers. The driving support information generation device of the present invention includes a processor to execute a program; and a memory to store the program which, when executed by the processor, performs processes of collecting vehicle information including traveling locus information indicating a traveling locus of at least one vehicle which travels a predetermined road section and generating cautionary information which is information to require a driver of the at least one vehicle to exercise caution when the at least one vehicle travels the section, on the basis of the collected vehicle information. The cautionary information is generated on the basis of variation in traveling of the vehicle.