Growing interest in character assessment along with a revolution in educational technology present an unparalleled opportunity for the field of character education. Drawing on our pilot work of the past two years and newly-developed Ecological Momentary Assessment (EMA) techniques, we propose to work with a talented interdisciplinary team of investigators and diverse set of middle schools in New England to conduct a 12-month longitudinal study of 500 students and their teachers, with daily assessments of Diligence, Honesty and Compassion. Our procedures will send daily questions to teachers and students, directly to their individual smartphones, that can be answered in seconds with the swipe or tap of a finger. We will conduct advanced statistical analyses of this extensive data, comparing our new methods to traditional measures of character and additional external data sources available within schools to validate and enhance measurement procedures. Major outputs are: 1) EMA assessment protocols for use by other researchers and schools; 2) three publication-quality manuscripts (one for each domain) describing the validity of these EMA procedures, 3) a rich de-identified longitudinal dataset for use by other researchers and 4) a set of training manuals to facilitate dissemination to other schools. This project will make an impact by: 1) by generating valid and feasible measures for use in real-world school settings; 2) improving evaluations of school-based character education programs (and helping separate the wheat from the chaff in this field); and 3) by providing an ongoing and effective means to monitor and routinely communicate about youth character development and, accordingly, elevate its place in the school setting. This progress, in turn, should help generate more effective methods of moral education, including the ability of educators to instill the "moral habits" that were so important to the life-success and influence of Sir John Templeton.