Cloud database migration can improve organizational performance in small and medium-sized enterprises (SMEs), but SME leaders are concerned about ineffective migration strategies, which can increase risks to data security, regulatory compliance, and operational continuity. Grounded in diffusion of innovation theory, the purpose of this qualitative pragmatic inquiry project was to explore the effective strategies SME leaders use to manage secure cloud database migrations, mitigate risks, enhance data security, ensure regulatory compliance, and improve organizational effectiveness. The participants were 10 SME leaders in the United States who had successfully adopted cloud-based database systems. Data were collected through semistructured interviews and publicly available documents. Through thematic analysis, three themes emerged from the findings: (a) strategic adoption of cloud-based platforms, (b) leadership-driven security governance, and (c) employee training and technology adaptation. A key recommendation is for SME leaders to implement formal cloud migration frameworks that include governance, security controls, risk assessments, employee training, and vendor evaluation. The implications for positive social change include the potential to achieve stronger data protection practices of consumer information, improved employee preparedness for digital transformation, and increased trust in secure business operations.