Vocational educators urgently need to keep learning throughout their careers. However, traditional professional development (PD), such as courses and workshops, yields limited transfer to the workplace as it does not align with how professionals naturally learn at work. The study discussed here reports on professional learning of vocational educators within one institute for technical vocational education in Western Canada. Seven instructors and five program chairs from five different programs were interviewed regarding professional learning in their departments, the extent to which this learning was enhanced through the implementation of an ePortfolio approach, and factors that contributed to or inhibited this learning. Our analysis shows that the ePortfolio approach increased some professional learning activities including goalsetting, documenting growth, discussions with peers, and reflection. Cross-case analysis illustrates that professional learning is embedded in professional practices and cannot be understood by examining individual factors separately from departmental environments. Based on our study, we can draw three conclusions: i) the interaction between the cultures in the original trade/profession and the vocational educational department is unique to the vocational education context and should be further explored, ii) the role of program chairs in vocational education is of crucial importance to instructor professional learning, and iii) our findings indicate that instructor professional learning practices are not static and can and should be improved. Further studies into and experiments with comprehensive approaches to supporting professional learning of vocational educators are necessary and long overdue.