This chapter considers two autoethnographic case studies as two teachers report on their journey towards making online learning more authentic, personal and humanized. One case study is a secondary school technology and applied science teacher and the other a tertiary history and literature lecturer. In both cases an initial reticence and even fear transitions into a journey of discovery with the online format. The importance of technical support, pedagogical support and administrative enthusiasm are seen as vital to a healthy transition to an online learning environment that maximizes the advantages of the technology. A link is drawn between humanizing the transition for teachers and humanizing the experience for students.