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Abstract Museums are local‐to‐global organizations operating in a digitized, distributed, and diverse 21st century world. Museums leaders face significant challenges in achieving broader relevance, meaningful engagement, and equitable outreach. This article examines the transformative potential of digitized collections to increase public engagement and enhance authentic educational efforts of museums, with specific emphasis on visual media as a key resource to achieve these outcomes. Using digitized collections to broaden learning opportunities and support a wide range of users will require museum leaders to engage in strategic digitization efforts—supplementing research images, making conscious decisions about meeting educational needs when setting digitization policies, and investing in meaningful outreach with digitized collections. Educational opportunities are contextualized with brief case studies of authentic investigations for middle school learners using digitized objects from a natural history museum. Three lessons learned during development and evaluation are described and implications for museum leaders are discussed.