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These challenges are often exacerbated when serving vulnerable communities with complex social needs. Despite these difficulties, technology holds the potential to help bridge the service gap, enabling these organizations to respond more effectively to the diverse needs of their communities. In our work, we conducted 21 semi-structured interviews with representatives from different community-based social service organizations in a mid-sized city in Northern Indiana. This city struggles with high rates of poverty and homelessness in several of its neighborhoods. Our findings revealed that although these organizations faced numerous technological challenges, data and knowledge management was a particularly significant issue. Based on our findings, we offer design recommendations for empowering community-based social service organizations and the people they serve through technology. 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