Shopify not calculating shipping price correctly on orders with multiple products

I have Shopify shipping by weight enabled, the product has a weight, and is configured with the correct box. In checkout, Shopify correctly calculates the shipping price when only ONE of the item is in the cart - $21.95.

If I add two to the cart, the shipping suddenly becomes LESS, at $16.90. WHY! A customer made an order and this happened, in the order details it shows that Shopify has the weight correct (image below), why is it calculating the shipping wrong?

image

What does that line say for a single item?

image

And how many packages do you have configured, and what are the dimensions/weights? Shipping and Delivery→Packages