Associativity is maintained for true primitives that are in the sketch and not for composite sketches such as shapes, sectioned topology, or sketch text.
The bug here is that you are able to select maintain association when selecting just a shape & sketch text, or at least not given a warning indicating that association will be not be maintained.
If you create a sketch that consists of say just a line segment and both a shape. Now do a project to sketch of the entire sketch and select maintain association. You will see the warning dialog that the shapes association will not be maintained as shown in the below attached image.
Thank you for pointing out the issue. I have logged this with development.