With the increase in popularity of online education for the K-12 learner, a door has been opened for new teaching opportunities. The changes brought about from this opportunity have also impacted the role of the teacher and the very nature of teaching. How though does a teacher educated in the traditional, face-to-face model know he or she is ready to teach in this new learning environment? How do teachers learn to teach online? The purpose of this study was to examine and understand how high school teachers describe the experience of learning to teach online courses. A qualitative, interpretive research design provided the framework for the study. A guided interview questionnaire, journaling of prior experience, discussions about K-12 online studies, and an exit interview were used to investigate the experiences of a group of online high school teachers who had made the transition from face-to-face to online instruction. The analysis of data revealed that online high school teachers faced struggles and frustration during the transformation that could have been alleviated with training and professional development prior to commencing the teaching position. Recommendations are made for the development of a systematic training program to improve online teaching pedagogy and an online practicum experience for teacher education programs that could improve the effectiveness of teaching online. In addition, further research is needed about the K-12 online teaching phenomenon to build the body of knowledge, influence stakeholders to better support online teaching staff, and ensure a successful transition for novice online teachers.