While social learning is not a new construct, we now have the ability to extend learning across place and time instantaneously with social media and digital tools. As we interact in new ways with multiple media we discover new approaches like transmedia learning, which leverages both social learning and social media. Transmedia learning is engagement-driven, learner-centric, unfolds across multiple media, and is designed to promote social learning. An I/ITSEC paper published in 2013 utilized the example of Warrior-Diplomat and was the first in a series introducing transmedia learning strategies to meet the demands of next generation learning. The present paper is the second in the series and expands on theories discussed in the 2015 I/ITSEC tutorial “Transmedia Learning in the Wild.� While the tutorial uses Warrior-Athlete as an example, the present paper departs from the tutorial and the 2013 paper by honing in on one aspect of transmedia learning—the practice of social learning as it applies to two approaches for preparing Veterans and transitioning Service members for the civilian workforce. In the spirit of the definition of transmedia learning provided above, conference participants who review the 2013 paper and attend both the 2015 paper and tutorial presentations will obtain unique and complementary information from each presentation about transmedia (social) learning in the wild, or as it naturally occurs in a cultural context. The present paper is divided into three sections. The first section introduces the need to retrain transitioning members of the Force and provides a description of the Instruction (DoDI) 1322.29 issued in 2014, titled "Job Training, Employment Skills Training, Apprenticeships, and Internships (JTEST-AI) for Eligible Service." DoD SkillBridge implements this instruction and is a Deputy Assistant Secretary of Defense (DASD) Force Readiness and Training initiative to connect transitioning Service members with civilian training opportunities. Semper Fi Odyssey, a 6-day intensive transition-assistance and career advancement program for injured veterans, is also presented to illustrate a range of social learning experiences presented as a continuum. The next section introduces three theories from learning science, cognitive psychology, and communication that support a social learning continuum. The theories support 5 key design features: Learning context, culture & community, calibration, and connections. The last section suggests a data collection plan for future measurement of digital engagement as it applies to transmedia (social) learning in the wild. Readers of the present paper will take away 5 key design features and unlock expanded content available online for a richer transmedia learning experience.