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Priya Shah, a new consultant, had just begun a project with Biko Taylor, Chief Procurement Officer for the City of Portland, Oregon. A few weeks before, on April 20, 2022, the Portland City Council had passed ordinance 276, authorizing Taylor to pilot inclusive contracting policies designed to attract small diverse businesses (SDBs). Taylor hoped this pilot would help foster wealth creation for marginalized demographic groups by providing more economic opportunities through government contracts. He wanted to identify policies and practices that his division could adopt to achieve the goal of awarding more city government contracts to SDBs. Shah wondered if she could bring her private-sector-sourcing expertise to help Taylor’s division improve its sourcing processes and mitigate the challenges in contracting with SDBs. What were some levers the city could use to increase representation of SDBs and incubate them as key suppliers? Were regulations and policies helping or hurting the city’s inclusive contracting goals? This field-based case details Portland’s procurement process, explores key stakeholders, and focuses on opportunities and challenges to increasing representation of SDBs in city projects.