Our paper reports findings from a two‑phase deployment of iPod Touch and iPad devices in a large, urban Canadian school board. The purpose of the study was to gain an understanding of the infrastructure required to support handheld devices in classrooms; the opportunities and challenges teachers face as they begin to use handheld devices for teaching and learning; and the opportunities, challenges and temptations students face when gaining access to handheld devices and wireless networks in K – 12 schools. A mixed method approach was used: online survey, monthly professional development activities with teachers, collected samples of lesson plans and student work, and regular classroom observations. Phase 1 findings (exploring only the use of the iPod Touch devices) suggest participants (students, teachers, and IT support staff) preferred a range of devices for a variety of commonplace tasks. They indicated they would select the iPod Touch for recording voices / sounds, listening to podcasts, and playing games. They preferred a laptop for searching the Internet, creating media, and checking email, and they selected paper or traditional options for drawing, reading, and tracking work / maintaining an agenda. Sixty percent had never used the device prior to the project. Despite that surprising finding, 70% of respondents felt it took less than hour to become familiar with it. However, this question did not probe comfort levels with the syncing / charging, iTunes’ account management side of use, and herein lay a challenge. In order to use personal devices in school settings, the school / district needed to create a common iTUNEs account and dedicate a computer to sync, share, and organize applications (apps), content, and system settings. This common account formed a “digital commons” of sorts; a place where participants had to negotiate what apps to share and permissions and access protocols. Participation in the commons required an ongoing exploration of what digital citizenship meant in classrooms and how this impacted teacher’s work, parental responsibility and changes in disciplinary approaches for administrators. Year 1 of Phase 1 yielded a wealth of data. Specifically, the iPod Touch devices were well received and well used by the majority of participants in the elementary and junior high settings. The high school students and teachers were more critical, as both appeared to struggle to find educational uses for the devices. Further, high school students initially appeared to “resent” the intrusion of school issued personal devices. Phase 2 continued to work with the Phase 1 participants and added the deployment of the iPad devices in three additional schools. Probably the most interesting finding was the lack of familiarity of these devices by all the participants. We anticipated many would have owned similar devices and be proficient in their use – this was not the case.