So, I have my store set up with a few different printers, Printify and Printful. They just have different items where neither has both.
I made a sale 10 min ago where they bought two hats and they got free shipping. I don't have free shipping on any hats, and I did a test checkout with one hat, shipping was normal first class. Then when I put two in the cart, I had free shipping all the sudden.