Disclosed is an operating system monitoring setting information generator apparatus including: a monitoring setting information management unit configured to store monitoring setting information used for monitoring of an operating system monitoring apparatus; a monitoring setting information output unit configured to generate a monitoring setting information file including the monitoring setting information stored by the monitoring setting information management unit, version information and binding information indicating a correspondence with a monitoring target software program, and to output the generated monitoring setting information file; and a digital signature unit configured to generate a digital signature of the monitoring setting information file, and to add the generated digital signature to the monitoring setting information file.