By 2040, it is estimated that more than 20% of the US population will be at least 65 years of age. Prevalence of chronic disease within this segment creates challenges and thus an opportunity for health care informatics to be of value through the use of remote automated tailored health coaching. Coaching can positively influence health behaviors and tailored health messaging has been shown to be more effective than generic or targeted communication strategies. The objective of this project is to demonstrate that it is feasible to develop an automated, tailored health messaging system that will enable health coaches to provide service to a significantly large number of patients than could be coached using conventional Internet tools alone.