I just realized there is something mysterious (at least for me) in the way you can add vertex instructions in Kivy with the with Python statement. For example,
There is nothing extra magical with the with statement, but perhaps you are unaware of how it works?
In order for any object to be used in a with statement it must implement two methods: __enter__ and __exit__. __enter__ is called when the with block is entered, and __exit__ is called when the block is exited for any reason.
What the object does in its __enter__ method is, of course, up to it. Since I don't have the Kivy code I can only guess that its canvas.__enter__ method sets a global variable somewhere, and that Rectangle checks that global to see where it should be drawing.