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Does anyone have any experience with TaxCloud? 

I have "Detect Automatically" selected on the Fiscal Position. 

However, when I add a product to the SO the taxes aren't automatically applied. 

I have to click "Update Taxes". 

Does anyone know how I get it to apply the taxes automatically?

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There is no configuration option to do this and we don't recommend customizing Odoo to support this.

During holistic testing when we first rolled this feature out, Users consistently preferred to have taxes updated on demand instead of during every change on a Sales Order or Invoice (new product, change in quantity, update of price).

The number of round trips needed to the TaxCloud API was reduced to only one. 

Users found the User Experience much better with an "on demand" design and we agreed with them.

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