Products In Multiple Categories

We have several products that are listed in multiple categories (dozens). If I setup a shipping method for 1 category but I purchase a product from a different category the shipping method doesn’t display, even though that same product also belongs to the category I’ve selected in shipping.

For example; say I have a t-shirt assigned to 2 different categories, T-Shirts and Red T-Shirts.

Then I setup a shipping rate for just T-Shirts. If I purchase the shirt from the T-Shirts category, everything works fine. But if I purchase the shirt from Red T-Shirts no shipping rates show up.

Is there a way to have this check all categories? I really don’t want to have to setup every category that a product may belong to since there are quite a few.