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As peer-delivered services are increasingly embedded within behavioral health organizations, a need has arisen to identify practices that facilitate supervision and support of peer providers. The authors present supervision strategies and lessons learned that emerged during a large pragmatic trial in three supportive housing agencies that examined a peer-delivered healthy lifestyle intervention for people with serious mental illness. Strategies included access to multiple supervisors, formal and informal support, acknowledgment of lack of role clarity, ongoing role negotiation, a collaborative approach to troubleshooting challenges, explicit emphasis on peer specialists’ value, and linking peer specialists to opportunities for mutual support and professional development.