We did experience nightmares with Windows Updates and looping issues; however, we got in touch with their tech support and they helped us configure our environment that the boot loops stopped immediately.
The key points where to make sure the workstations are online by setting a WOL task; then to make sure they don't go into Standby / Sleep when the updates are getting installed and also make sure to use the caching of Windows Updates for faster installation.
We've got two sites with Deep Freeze and one of them downloads the updates from the Internet and other uses a WSUS server, both environments have been working fine since the last couple of versions and the recommended settings.
Give it a shot or get in touch with their tech support – they are amazing.