Despite the documented importance of professional experiences in teacher preparation, numerous questions persist as to how university supervisors can effectively contribute to rural preservice teachers' development and to establish lasting collaborations between involved stakeholders (e.g., collaborating teacher, principal, community). This paper provides insight into the challenges and potential for a comprehensive and updated approach to in-person supervision in a rural sociocultural context. Transcriptions of field notes, observation protocols, and conversations from forty supervision travels to remote Alaska villages are examined and interpreted. Results support a fresh, rural-contextual approach to in-person supervision that has the potential to help preservice teachers not only master effective teaching strategies but also support teacher recruitment, retention, and collaboration.