For teachers in the 21st century it is become critical that they develop the skills to be able to teach in a world that is being transformed by technological innovations. These skills include effectively teaching in blended learning environments with high-quality online learning resources available on the internet. Chief among the challenges faced by these teachers is that mid- and late career teachers, unlike pre-service teachers, do not have adequate technology knowledge. A challenge for pre-service teachers is that they do not have the pedagogical and content knowledge to be able to effectively implement their technology knowledge in the classroom. This retrospective comparative case study was undertaken to understand reciprocal mentoring (RM) relationships that can occur between in-service teachers and pre-service teachers during implementation of a technology based lesson. The transfer of knowledge between the members of the RM dyad is described through the lens of technological pedagogical content knowledge.