This study ambitiously foregrounds for Ontario school districts key elements that need to be embedded in a professional development plan in order for classroom teachers to successfully integrate technology into their classroom curriculum. The research conducted followed the case study and action research models based on my direct relationships with four teachers and their experiences in receiving professional development support in order to integrate technology into their classroom curriculum. My role in providing professional development varied in format and degree but was consistently based on the individual needs of the teacher. The individual case studies narrate each teacher's journey of professional development over the course of an academic year based on data gathered through interviews, surveys, observational field notes, and a quantified empirical rubric. Data pertaining to the professional development initiatives undertaken by several Ontario school districts is also presented. Hence, this study brings to the foreground key factors to consider when planning professional development opportunities for teachers.