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Little problem regarding an object I want to wrap based on two others

So, if you can see that rectangular object “cube”, what I want is firstly to wrap it around that cylinder there. However, when it meets that more complex round object, which is actually an Illustrator spline from the beginning, it’s supposed to follow that. Since it’s not a flat surface, I want it to be wrapped around that as well, so that the objects blend together. If you don’t understand what I mean, think about an Omega symbol or look at this picture:
I have taken a look at spline wrap, but not only am I still not entirely getting its function, I also have two objects to consider. What would be the easiest solution to this?