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We wish to add a product to more than one category. Would we need to enter the product twice to do this or can we add a single product to multiple categories?
No, you can easily add products to more than one category. When creating or editing a product, there is a multiple dropdown menu listing the categories. You can add the product to any of these categories by holding down the Ctrl key (on a PC) or the 'Apple' key (on a Mac) and single clicking the categories. You should see each one you select in this way highlighted.