Incorrect Shipping Rates for Items under 1 lb

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I apologize if this is already posted somewhere but this is an issue that has plagued our account for over half a year now. I tried searching for a similar issue in the forum but have not found a solution.

The only shipping rules we have established is based on the product weight. We only work with customers living in the USA due to keeping our shipping simple. When customers order our products that are under 1 lb, the shipping is set to be $5 (please see referenced graphic below). However, customers are constantly being charged $11 shipping for something that costs a lot less than $11 to buy (also referenced below). The shipping cost keeps falling into the "Standard Medium Box" instead of the "Standard Small Box". This has deterred a few customers from ordering from us due to the excessive shipping charges as demonstrated by abandoned carts.

Could someone please help explain how might I fix this issue? 


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