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This article employs a boundary work framework to analyze how volunteers from two nonprofit human services organizations navigated the tensions between volunteerism and professionalism. Based on interview data and analysis of organizational documents, the study found that volunteers at the first organization dichotomized volunteerism and professionalism as incompatible social systems with divergent objectives, practices, and tools. Volunteers at the second organization engaged in constant boundary crossing, oscillating between a volunteer and professional approach to tasks and relationships depending on the context. In both cases, paid staff and members of the public impacted participants’ ability to engage in boundary work. The study offers insights for non-profit organizations wishing to professionalize their volunteer workforce by specifying how volunteer job types, organizational structure, and interactional partners' feedback impact volunteers' ability to engage in boundary crossing, passing, and boundary spanning.