This study explores factors that influence teachers' development of culturally sustaining pedagogical practices. The research is guided by the question: How do teachers perceive their development of culturally sustaining pedagogical practices? Data collection occurred during the fall 2020 semester and involved five high school teachers. Given COVID-19 and the pervasiveness of online learning, interviews and observations occurred via Zoom. The data includes semi-structured interviews, fieldnotes, teaching artefacts, and questionnaires. This study found that all teachers employed dynamic support systems that significantly factored into their development as culturally sustaining educators. Due to the central role of communities of practice in participants' development, a communities of practice model for culturally sustaining teacher development was created and illustrated in this paper. Social interaction played a significant role in developing educators' critical stance towards teaching -- demonstrating possibilities to productively relate culturally sustaining pedagogy and communities of practice for a critical communities of practice lens to teacher learning. This study suggests that a collective orientation should be central to the work of preservice and in-service teachers within teacher education programmes and PK-12 schools.