One method underutilized in training teachers to use technology is to use live modeling sessions. This study qualitatively investigates how the use of modeling sessions impacted students. In this study we found that modeling was perceived by most students to be effective at teaching technology skills and ideas for integrating technology as teachers. However, we identified several breakdowns in the ability of students to transfer their understanding of technology integration to their own situations. We explain this difficulty of transfer of learning and describe five situations when these breakdowns were likely to occur. Implications include the benefits of using live modeling if adapted to address students’ unique needs, as well as future research into the impact of contextual differences on the transfer of students’ learning.