Organizations invest a significant amount of time and money on management and supervisory training programs. The intent of this study was to examine the relationship between four specific work-environment factors (organization support, supervisor support, peer support, and participation in a peer support network) and transfer of training at one-month, six-month, and one-year points following supervisory skills training. Quantitative and qualitative data were collected from both trainees and their direct supervisors. ANOVA results of aggregate data showed that trainees who reported receiving high levels of organization, supervisor, and peer support, and who also participated in a peer support network, reported higher levels of transfer of knowledge and skills. When data were segregated and examined according to length of time since trainees had completed training, findings were still significant for organization, supervisor, and peer support but only at the one-year point, not at one month or six months. Participation in a peer support network was not significant at any of the three points of time. In short-answer responses, trainees indicated that lack of time and lack of management support and buy-in were significant barriers to transfer. T-test results indicated that trainees and their supervisors did not differ in their perceptions of level of transfer of skills or amount of organizational or direct supervisor support received by the trainees.