Simulating thick cloth, objects not following mesh deform cage

I am really sorry if this is a noob question, but I am trying to follow this tutorial in simulating thick cloth:

However, after the step where I bind my object to the mesh deform cage (which has a cloth simulation on it like in the video), my object does not follow the mesh deform cage like it does on the video.

I did a quick test on this using simple shapes and could not get it to work:

But originally I wanted to use this method on my project of animated scales with notes, and use the cloth simulation to make the scales flow and move like cloth:

Any help with this would be greatly appreciated! Thanks!