With the aim of assessing the use of intelligent tutoring technology for math teaching in Chilean public schools, an experimental study was performed in the period 2013-2014. Although it was a successful experience in terms of number of participants and learning outcomes, it was not achieved without a number of difficulties which could be explained by focusing on the cultural challenges encountered in the endeavor. In this paper we explore the impact of cultural dimensions such as: organizational strategies and structure; organizational culture; pedagogical processes, human resources, and technology deployment. We characterize each one of these aspects by means of a qualitative study of the implementation process, involving tasks such as planning and technical support, class observations, interviews, and support to teachers in the classroom and lab. As a result, we propose a Diagnostic Chart which could help in the identification of pre-conditions to be solved at an earlier stage of th...