Educators who introduce critical socio-ecological issues into learning contexts often experience formidable internal and external challenges. This is especially true when intersecting Indigenous and environmental issues are involved. Compounding such difficulties in Canada is an inadequate level of pre-service, curricular, resource, and research support in this area. As such, while an increasing number of bold educators are incorporating discussion of Indigenous environmental issues, activism, and related history, law, and policy into their teaching practice, many others are interested, but remain understandably reticent. This study explored the experiences of educators in a variety of contexts across Canada with attempting to incorporate critical consideration of Indigenous environmental issues into their teaching practice. Findings include discussion of challenges encountered, successful strategies employed, the societal significance of these considerations, and future research possibilities.