To reduce the chance of sysprep or deployment issues, please follow the recommendations listed in our System Image Best Practices knowledge base article.
It is important to take a snapshot or capture your image master before running Sysprep in case you run into any problems.
The Sysprep Executor included with the Sysprep Creator utility has the ability to check some of the most common items that may cause Sysprep to fail as well as a few best practice items.
Here are some examples of upgrades that will cause sysprep to fail:
Windows 7 > Windows 8
Windows 8 > Windows 8.1
Windows 10 version 1507 > Windows 10 v1511
Beginning with Windows 10 version 1607, Sysprep can be used to prepare an image that has been upgraded, more information here