Hi @paul.grothe1998,
I see that you are visiting as a new member to the AutoCAD Mechanical forum. Welcome to the Autodesk Community!
Thank you for providing the files. They appear to be from version 2019, so I tested in that version. Both blocks appear to be functioning and updating dimensions the same with the grips I tested.
One thing I did see that may or may not be intentional is that the grips on the left are based on a fixed diameter, and only change the thickness of the perimeter (to the inside or outside of the diameter). This could be affecting the measurements not changing. See screen shots below:


If this is as intended, or I have missed something, providing a ScreenCast of your workflow and what you are seeing, would help us narrow down the cause of the issue.
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All the best,
Cheryl Buck
Technical Support Specialist

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