Much contemporary teachers’ work is located at the interface of complex systems of policy and provision. That interface is increasingly the site of broader discursive tensions as change is enacted, with profound implications for individual classes and courses. If pedagogies are to be engaging in such a context, teachers need to be simultaneously facilitators and facilitated. Yet often those teachers are at both the forefront and the frontline of educational change, without sufficient ammunition in their armoury as they battle to enhance students’ learning outcomes and find meaning in their work.The paper illustrates this argument by reference to two cases of engaging pedagogies and facilitating pedagogues: graduate research students working as novice online tutors in a Masters management program; and experienced secondary teachers implementing new vocational education subjects for senior secondary students in schools in a Queensland regional community. Deploying the concept of communities of practice (Wenger, 2000; Yamagata-Lynch, 2001), the paper traces some of the professional and personal challenges experienced by both groups of educators, as well as their respective strategies for making the pedagogies engaging for their students. They gain from these communities the support that is often absent from the systems that employ them.