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I'm trying to figure out how to charge tax on shipping to only a select list of states where state law requires tax on shipping.

I currently have one list of Tax Rules in Magento (provided by Zip2Tax) that has a rule for each zip code in the country.

How can I accomplish this?

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Tax is a very complex area, and there are definitely limitations with what you can do in Magento raw. There are solutions out there that we see in use, for instance Avalara and Taxjar.com.

You can though set the shipping to use the 'shipping' tax class - this is set under System->Configuration->Tax. Then in the tax rules you can set up separate taxes for the shipping amount only. There is the ability to define tax rules down to the zipcode level.

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