Abstract Wikis have the potential to change learning environments from traditional knowledge transmission models to knowledge transformative ones where students generate, share, and reshape knowledge. In this three-part study, graduate students created wikibooks across institutional settings. One of these projects extended to universities in China, Taiwan, Malaysia, and the United States, whereas the other two involved two universities in the United States. The degree of scaffolding and other support varied in each project. At the end of each study, students were surveyed about their wikibook efforts. In addition, instructors across the institutions were interviewed about the obstacles they faced as well the opportunities. Based on these results, more than two dozen cross-institutional wikibook issues are organized into five key themes: (1) instructional issues; (2) collaboration issues; (3) technology issues; (4) constructivism and sense of community issues; and (5) wikibook issues. Several recommendations are offered related to the use of wikibooks in the classroom as a transformational learning tool.