The present technology relates to an information processing system, a recording medium, and an information processing method that make it possible to transmit an action suitable for a context of a user to the user in a natural way. An information processing system according to an aspect of the present technology acquires context information representing at least one of a surrounding environment of a user having a device, a feeling of the user, a situation of the user, feelings of other people around the user, or situations of the other people, recognizes a context of the user on the basis of the context information, determines an action corresponding to the context, and determines a transmission method for the action to the user, the transmission method being suitable for the context and the action. The present technology can be applied to a wearable device worn by a user.