An information processing apparatus comprising: a data processing unit configured to receive driver's biological information and evaluate a wakefulness degree of a driver, wherein the data processing unit is configured to analyze at least one of behaviors of an eyeball or a pupil of the driver and is configured to evaluate the wakefulness degree of the driver by applying the behavior analysis result and a wakefulness state evaluation dictionary that is specific for the driver and has been generated in advance, wherein the data processing unit is configured to evaluate the wakefulness degree of the driver by using the wakefulness state evaluation dictionary specific for the driver that is generated as a result of learning processing based on log data of the driver's biological information, wherein the data processing unit includes a learning processing unit that is configured to execute learning processing by analyzing a log obtained by monitoring processing for acquiring the driver's biological information, to evaluate the wakefulness degree of the driver, and to generate the wakefulness state evaluation dictionary specific for the driver, characterized in that the learning processing unit is configured to execute learning processing that acquires and uses teacher data at the normal time that is driver's state information when it is possible to normally start manual driving and teacher data at the abnormal time that is driver's state information when it is not possible to normally start manual driving on a basis of the operation information of the driver at the time of return from automatic driving to manual driving. a data processing unit configured to receive driver's biological information and evaluate a wakefulness degree of a driver, wherein the data processing unit is configured to analyze at least one of behaviors of an eyeball or a pupil of the driver and is configured to evaluate the wakefulness degree of the driver by applying the behavior analysis result and a wakefulness state evaluation dictionary that is specific for the driver and has been generated in advance, wherein the data processing unit is configured to evaluate the wakefulness degree of the driver by using the wakefulness state evaluation dictionary specific for the driver that is generated as a result of learning processing based on log data of the driver's biological information, wherein the data processing unit includes a learning processing unit that is configured to execute learning processing by analyzing a log obtained by monitoring processing for acquiring the driver's biological information, to evaluate the wakefulness degree of the driver, and to generate the wakefulness state evaluation dictionary specific for the driver, characterized in that the learning processing unit is configured to execute learning processing that acquires and uses teacher data at the normal time that is driver's state information when it is possible to normally start manual driving and teacher data at the abnormal time that is driver's state information when it is not possible to normally start manual driving on a basis of the operation information of the driver at the time of return from automatic driving to manual driving.