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Nudging provides a way to gently influence people to change behavior towards a desired goal, e.g., by moving towards a healthier or more environmentally friendly lifestyle. Personalized and context-aware digital nudging (named smart nudging) can be a powerful tool for efficient nudging by tailoring nudges to the current situation of each individual user. However, designing smart nudges is challenging, as different users may need different supports to improve their behavior. Determining the next nudge for a specific user must be done based on the user’s current situation, abilities, and potential for improvement. In this paper, we focus on the challenge of designing the next nudge by presenting a novel classification of nudges that distinguishes between (i) nudges that are <i>impossible</i> for the user to follow, (ii) nudges that are <i>unlikely</i> to be followed, and (iii) <i>probable</i> nudges that the user can follow. The classification is tailored to individual users based on user profiles, current situations, and knowledge of previous behaviors. This paper describes steps in the nudge design process and a novel set of principles for designing smart nudges.