Here is a fantastic post by Cliff Jones (Microsoft Consulting Services) with a great solution to address the ever cumbersome multiple issue while executing a Task Sequence.
Today’s blog post goes behind the scenes to talk about how to prevent installing all published Windows Update’s which require multiple reboots to successfully install, during a ZTI deployment Task Sequence. These updates can cause issues as a result of the following behavior; the Task Sequence engine is aware the update requests the initial reboot. Upon boot-up, the Task Sequence engine never initializes and therefore can’t be aware that the same update is requiring a second reboot, and thus finally won’t make the necessary changes to restart the TS engine again. When the second reboot occurs, during the deployment, the TS will be in an erroneous state, and will cause an error similar to:
"Task Sequence environment not found"
Ideally, these updates should be injected using DISM during the Offline phase of installation, or added during the Build and Capture as the LTI process is not affected by these updates. Either way, a detection and blocking mechanism is needed for your ZTI deployment process.