The paper discusses best practice approaches and metrics for evaluation that support seamless learning with social media. We draw upon the theoretical frameworks of social learning theory, transfer learning (bricolage), and educational design patterns to elaborate upon different ideas for ways in which social media can support seamless learning. To exemplify how social media can support seamless learning we follow up with presenting three case studies on the organizational level, on the program level, and on the individual level. Each case study analyzes the context for the use of social media, followed by a discussion of how social media serves as a catalyst for seamless learning.