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For vocational and professional education (VPE) to remain relevant, instructors need to keep developing themselves and their practices. Supports for instructor learning have traditionally included formal training and conferences. However, much instructor learning happens on-the-job. The present study situates instructor learning in the context of departmental practices, focusing on structural, cultural, and leadership conditions for learning. A multiple case mixed-method approach was used, collecting data from five departments across three institutes for VPE in western Canada. Findings show that instructor collaboration, sharing materials, mutual reflection, and leadership actions contribute to instructor learning. Findings also illustrate how beliefs and practices prevalent in instructors’ original trade/profession influence instructor learning. Insights will help practitioners in VPE transform practices in support of instructor learning.