Blogs, wikis, podcasting, and a host of free, easy to use Web 2.0 social software provide opportunities for creating social constructivist learning environments focusing upon student-centred learning and end-user content creation and sharing. Building on this foundation, mobile Web 2.0 has emerged as a viable teaching and learning environment, particularly with the advent of the iPhone (nicknamed “the Jesus phone”) and iPod Touch. Today’s wifi enabled smartphones provide a ubiquitous connection to mobile Web 2.0 social software and the ability to view, create, edit, and upload user generated Web 2.0 content. This chapter explores the potential of wireless mobile devices and Web 2.0 (social software) to create social constructivist learning environments that bridge multiple learning contexts. The chapter provides an overview of current literature in the field, and discusses the pedagogical design of six example mobile Web 2.0 trials undertaken during 2007 and 2008 as part of research into the potential of mobile Web 2.0 to enhance tertiary education. The trials were based in three different courses and illustrate the application and integration of mobile Web 2.0 to bridge a range of learning contexts. The chapter argues that wireless mobile devices can be used to intentionally create disruptive learning environments that facilitate a social constructivist approach to teaching and learning.