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This paper explores how playful professional learning experiences can challenge conventional notions of assessment, particularly regarding the cultural and linguistic diversity of learners. Traditional teacher training often emphasizes standardized testing and accountability, overlooking the fundamental process of evidentiary reasoning that undergirds assessment. Our study investigates "Assessment Party," a professional development (PD) game where teachers role-play different aspects of the assessment process. Preliminary findings indicate this playful approach to PD encourages educators to reflect deeply on their practice and consider how assessment can be designed for fun and to support diverse ways of knowing. We highlight the potential of playful PD to surface critical perspectives on assessment practices, fostering a more equitable educational environment.