Check & Connect (C&C) is a targeted prevention program developed in the United States and proved efficient for students at risk of school disengagement and dropout. A research team from Montreal (Canada), using a randomized controlled trial design, conducted an effectiveness study of C&C (renamed Motiv’Action in French), in secondary schools (2012–15). Based on the very promising early results, a French school district (Académie de Rouen) asked the University of Montreal to launch another effectiveness study in France with middle school students (2014–17). Both experiments investigated, to varying degrees, the organizational and human factors related to the implementation of the program and relations with the observed effects. This chapter synthesizes the different findings on the challenges and facilitators encountered in the implementation of C&C in Francophone schools in Canada and France.