There is provided a work machine information processing device including a risk detector configured to detect a risk relating to a state or a surrounding environment of a work machine, notifier configured to notify an operator of the work machine of the risk detected by the risk detector, behavior detector configured to detect a behavior of the operator after the notification of the notifier, and calculator configured to calculate a safety behavior evaluation value obtained by quantitatively evaluating the behavior of the operator in terms of a degree of contribution to the safety, based on contents of the risk detected by the risk detector and the behavior of the operator detected by the behavior detector.