Disruptive technologies developed in the digital age expose individuals, businesses, and government entities to potential cyber security vulnerabilities. Through the conceptual framework of general systems theory, this multiple case study was used to explore the strategies among owners of 4 retail small- and medium-size enterprises (SMEs) in Melbourne, Florida, who successfully protected their businesses against cyber attacks. The data were collected from a review of archival company documents and semistructured interviews. Yin's 5-phased cycles for analyzing case studies provided the guidelines for the data analysis process. Three themes emerged from thematic analysis across the data sets: cyber security strategy, reliance on third-party vendors for infrastructure services, and cyber security awareness. The study findings indicated that the SME owners' successful cyber security strategies might serve as a foundational guide for others to assess and mitigate cyber threat vulnerabilities. The implications for positive social change include the potential to empower other SME owners, new entrepreneurs, and academic institutions with successful cyber security strategies and resources to affect changes within the community. SME owners who survive cyber attacks may spur economic growth by employing local residents, thus stimulating the socioeconomic lifecycle. Moreover, implementation of these successful strategies may catalyze consumer confidence, resulting in greater economic prosperity.