At the end of the 2010-2011 school year, San Diego Unified School District, had 10,000 iPads in use and was set to add 18,000 more the next semester. Teachers and students were enthusiastic about using the devices yet the district faced a serious problem: Teachers were reporting to the instructional tech team that using Apple Configurator and mobile sync stations to add new content to 30 iPads at a time was not working well. Like San Diego, school districts around the country are realizing that managing tablets brings a host of new and time-consuming headaches. "T.H.E. Journal" interviewed several district tehnology leaders in charge of large tablet deployments about their deepest pain points during implementation, and this article discusses what they had to say.