I had a similar problem when I updated to Configurator 2. I resolved the issue by 'purchasing' all the apps through the Volume Purchase Program which then allowed Configurator 2 to install them without requiring an Apple ID each time. This applies to free apps as well as paid apps. Just be sure in Configurator 2 you are signed in using the proper VPP account in the STORE tab.

• Using Apple Configurator 2
• App Configurator 2 Mac Installer

The app can be used to configure large numbers of devices with specific settings, apps, and data for students, employees, or customers. Apple Configurator 2 is free on the Mac App Store. To use the new Configurator, just download the archive for your platform, extract/open and run the app. There's no installer yet or auto-update features, so you'll have to retain archive contents for future use and download a new version when it comes out. Configurator is now built for all major platforms as a standalone app.

Configurator 2 then assigns licenses of each app (even the free ones) to each iPad. Be sure to 'buy' enough licenses of the free apps to cover your fleet of iPads.

I hope this helps.

Mark Sheward

Oct 27, 2015 7:42 AM

Apple Configurator makes it easy for anyone to mass configure and deploy iPhone, iPad, and iPod touch in a school, business, or institution.

Three simple workflows let you prepare new iOS devices for immediate distribution, supervise devices that need to maintain a standard configuration, and assign devices to users. Quickly update your devices simultaneously to the latest version of iOS, configure settings, and install apps and data for your students, employees, or patrons.

Apple Configurator can be used by larger organizations and businesses to set up new devices, install enterprise apps, and enroll each device with a Mobile Device Management solution for remote management by an IT administrator. It is perfect for the classroom or student lab where devices need to be quickly refreshed and kept up to date with the correct settings, approved policies, apps and data. Apple Configurator can also be used to personalize devices with data and documents for specific users.

Prepare devices

• Configure multiple devices simultaneously
• Update devices to the latest version of iOS
• Create and restore a backup of settings and app data from one device to other devices
• Import apps into Apple Configurator and sync them to new devices*
• Use the built-in editor to create and install iOS configuration profiles
• Enroll devices with your Mobile Device Management solution for remote management

Supervise devices

Using Apple Configurator 2

• Organize supervised devices into custom groups
• Automatically apply common configurations to supervised devices
• Quickly reapply a configuration to a supervised device and remove the previous user’s data
• Import apps into Apple Configurator and sync them to supervised devices*
• Define and apply common or sequential names to all devices
• Restrict supervised devices from syncing with other computers

App Configurator 2 Mac Installer

Assign devices

• Add users and groups manually or autopopulate via Open Directory or Active Directory
• Check out a device to a user and restore the user’s settings and data on that device
• Check in a device from a user and and back up the data for later use, possibly on a different device
• Apply custom text, wallpaper, or the user’s picture to a device’s Lock screen
• Import and export documents between your Mac and Apple Configurator
• Sync documents between assigned devices and Apple Configurator

What's New:

• Support for new hardware
• Compatibility fixes for OS X 10.10.3
• Support for new configuration profile payloads and settings introduced in iOS 8.1.3, 8.2, and 8.3
• Restrictions: Force Apple Watch wrist detection
• Restrictions (supervised only): Allow modifying Touch ID fingerprints, Allow predictive keyboard, Allow auto correction, Allow spell check, Allow Define
• VPN: New IKEv2 cert and encryption keys and values