The present technology relates to an information processing apparatus, an information processing method, and a program which are possible to enable the user to reliably avoid a risk. The information processing apparatus includes a presentation control unit that generates a risk avoidance proposal for a user on the basis of a predicted risk, an evaluating unit that evaluates a level of obedience of the user on the basis of response of the user to the risk avoidance proposal, and a risk predicting unit that adjusts a risk prediction parameter on the basis of the evaluated level of obedience. The present technology can be applied to, for example, an information processing system or an information processing apparatus which assists driving of a mobile body, or an information processing system or an information processing apparatus which provides various kinds of insurances.