To determine if Apple Configurator will work for my company's needs, I have been testing it with my personal iPad. After hours of testing and reading through documentation, I have 3 questions about using Apple Configurator to install a free app onto iPad. Question 1: In-use iPads I have been unsuccessful in using Configurator to install a free app onto my personal 1st-gen iPad. No matter what I try, I get this error message: Apple ID not authorized. Is there any way to use Configurator to install a free app onto an iPad that has previously been associated with an Apple ID? Question 2: Brand-new iPads My company needs to install a free app onto 300 new 3rd-gen iPads. Because my tests failed, I don't know if Configurator will actually help us with this task. Can Configurator be used to simply install a single free app onto a bunch of brand-new iPads? Question 3: Deleting & redownloading the app The guide Deploying iPhone and iPad: Apple Configurator (apple.com/iphone/business/docs/iOS_Apple_Configurator_Mar12.pdf) says on page 3: To update apps deployed using Apple Configurator, you must reconnect to the same Mac from which the apps were installed. Additionally, you cant redownload these apps via iTunes in the Cloud. [emphasis added] Our goal is to install the free app onto the 300 iPads and then never to connect these iPads to Apple Configurator again. If the individual users want to update the app, they will need to delete the app and then redownload it from the App Store using their own Apple IDs. Is it possible to delete a Configurator-installed app and then redownload it using a personal Apple ID?