The purpose of this mixed methods sequential explanatory study was to explore how specific dimensions of supervisor support (mentoring, coaching, social support, and task support) influence the transfer of learned knowledge and skills to the job. Quantitative data were collected from employees (N = 48) who develop curriculum at an educational organization and analyzed using multiple regression analysis; this was followed by in-depth interviews (n = 10) that focused on participants’ lived experiences of supervisor support, transfer motivation, and training transfer. Findings suggest that mentoring, coaching, social support, and task support directly and/or indirectly facilitate training transfer and provide greater insight into the underlying mechanisms that account for how and why supervisor support influences training transfer.