In recent times issues of sustainability and place, and human connectedness and care for outdoor environments, have been the subject of increasing professional dialogue in outdoor education in Aotearoa New Zealand. Attention has been drawn to the ways in which traditional, adventure-based conceptualisations of outdoor education shape pedagogical practice in particular ways, potentially obscuring opportunities to explicitly promote student connectedness to, and learning about and for the outdoors. This paper contributes to this evolving dialogue about the greening of outdoor education by specifically targeting assessment in senior school outdoor education. By initially establishing the interdependence of curriculum, pedagogy, and assessment, the potential that assessment has to constrain and/or drive this recent curriculum and pedagogical re-prioritising in outdoor education is made evident. We argue that it is possible for assessment to be a productive engine for student learning about sustainable relationships with the outdoors. Five interconnected catalysts are highlighted as being central to this: (i) the alignment process, (ii) using fresh eyes with current achievement standards, (iii) taking another look at curriculum in relation to assessment, (iv) writing programme-specific assessments, and (v) reflective decision making. These are suggested to be key considerations for outdoor educators for the potential of school-based outdoor education to be fully harnessed.