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What if your site is a large ecommerce site?  I'm working with someone who just had their site rebuilt and none of their pages fall into a hierarchy category>category options> product.  You go to the category page and then when you go to another, your url extension is completely unique.  Is this going to hurt them in the long run? Keep I'm already having them change some of the URLs because they are useless extensions that don't match the pages and are no good for SEO that way. Should they seriously consider restructuring too? Thanks!