Various approaches enable automatic communication generation based on patterned behavior in a particular context. For example, a computing device can monitor behavior of a user to determine patterns of communication behavior in certain situations. In response to detecting multiple occurrences of the certain situation, a computing device can prompt a user to perform an action corresponding to the pattern of behavior. In some embodiments, a set of speech models corresponding to a type of contact is generated. The speech models include language consistent with patterns of speech between a user and the type of contact. Based on context and on the contact, a message using language consistent with past communications between the user and contact is generated from a speech model associated with the type of contact.