The editorial by Bull et al. (2008) on connections between informal and formal learning made explicit one element of solving what Koehler and Mishra (2008) termed a "wicked problem." This wicked (complex, ill-structured) problem involves working with teachers for effective integration of technology in support of student learning. The technology, pedagogy, and content knowledge (TPACK) model suggests that some individuals may have expertise in technology, some may have expertise in pedagogy, and some may have content area knowledge, yet real success can be anticipated only at the convergence of all three areas of expertise (Bull et al., in press). Bull et al.'s editorial reminds us of the importance of sociocultural context in implementing any instructional approach or professional development model--a context that should connect to and, where possible, take advantage of innovative technologies, including "emergent social media and communications technologies." The editorial prompted our own discussion of K-12 and preservice programs that had already connected informal and formal learning, and it challenged us to consider some essential conditions for supporting classroom applications of Web 2.0 technologies.