When your Microsoft Deployment Toolkit (MDT) client displays the big red “Operating System Deployment did not complete successfully” error message, dread sinks in.

You have MDT setup and deploying in your environment. Everything is going perfect until your Task Sequence or Custom Settings file gets changed. Now you are getting a bunch of cryptic errors or just the general constant reboot error! Let’s look at the top reasons why a MDT Task Sequence fails.

“Operating System Deployment did not complete successfully”

Operating System Deployment did not complete successfully

This problem, documented in the MDT 2013 Preview release notes, occurs when the critical task “Install Operating System” is modified in the Task Sequence. Normally, this task is modified when you are replacing or upgrading your primary enterprise operating system. For example, changing your primary task sequence to deploy Windows 8 instead of Windows 7.

Changing the OS within my Task Sequence

Changing the OS within my Task Sequence

Another less common example is changing the deployed OS from one architecture to another within the same task sequence. By naming your Task Sequence and ID after the OS being deployed, you can discourage this mistake.

As a best practice, create a new task sequence when you need to deploy or replace an older operating system. If you’ve modified or added extra tasks, you can copy and paste them into your new task sequence. If you have a lot of changes in a single group (such as in the State Restore group), you can simply copy the entire group into your new Task Sequence.

Copying the State Restore group

Copying the State Restore group

By right clicking on any group, you can copy it. Right click on the last group and select paste. You can then use the Up/Down arrows to move the group around in the task sequence. After you have your new task sequence created, you can remove your (older) task sequence that deploys your old operating system.

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