This paper presents a comprehensive and practical framework for automatic generation of real-time tailored messages in behavior change applications. Basic aspects of motivational messages are time, intention, content and presentation. Tailoring of messages to the individual user may involve all aspects of communication. A linear modular system is presented for generating such messages. It is explained how properties of user and context are taken into account in each of the modules of the system and how they affect the linguistic presentation of the generated messages. The model of motivational messages presented is based on an analysis of existing literature as well as the analysis of a corpus of motivational messages used in previous studies. The model extends existing ‘ontology-based’ approaches to message generation for real-time coaching systems found in the literature. Practical examples are given on how simple tailoring rules can be implemented throughout the various stages of the framework. Such examples can guide further research by clarifying what it means to use e.g. user targeting to tailor a message. As primary example we look at the issue of promoting daily physical activity. Future work is pointed out in applying the present model and framework, defining efficient ways of evaluating individual tailoring components, and improving effectiveness through the creation of accurate and complete user- and context models.