We present the development of the user interfaces of a multi-device digital coaching service that provides tailored feedback to users concerning their physical activity level and medication intake. We present the outcomes of a survey study of user preferences regarding the situation, device and timing of feedback they receive from their personal attentive digital coach. There are clear preferences among the subjects for different types of messages on different devices. Results were implemented in a first prototype. We present the results of a user evaluations with a real version of the digital health coach and we compare them with the results of the survey study.