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Overall, 11% of high school students leave school without a diploma, and the percentage is higher for at-risk populations. High school graduates earn higher salaries and are healthier and more law abiding than dropouts. Research is limited on the motivation of at-risk students to graduate from high school related to their technological identity to include technology and social media in their learning schema. This qualitative case study explored at-risk studentsâ?? perceptions of social media, personal learning networks, and informal learning in facilitating their graduation. Pinkâ??s concept of motivation, Siemensâ??s connectivism theory, and Bingham and Connerâ??s theory of engagement and social learning provided the conceptual framework. Interviews were conducted with 11 at-risk students identified by one Charter school: 4 students at-risk of dropping out, 3 dropouts planning to return, and 4 dropouts who had returned to high school. Open coding was used to identify rich themes and patterns that may help at-risk students succeed in school. Of the 5 themes identified 4 related to technology identity: transference to learning, relationships with personal learning communities and social networks, bridging technologies, and connected knowledge. Relationships with instructors and the school community also emerged as a theme. Connecting familiar and accessible technologies with formal learning could provide additional means of supporting academic success. Permitting the use of smart phones and social media to provide technological access to learning materials and instructors may create a motivating learning environment where students are willing to remain in high school to obtain a degree. Potential social and work benefits beyond high school may accrue for students.