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I'm not sure if this is possible or not, but here is what I'm trying to achieve. I'm using WooCommerce, and I have it setup to prepend a base slug and the product category to my product permalinks. So, my product permalinks look like this:

example.com/shop/%product_category%/%product_slug%

Now, I want to create another post type called "gemstone" that uses the shop base page in its permalinks, so they would look like this:

example.com/shop/gemstone/%gemstone_slug%

The problem is that all of the gemstone pages 404. This is because their URLs are rewritten so that "gemstone" is assumed to be the %product_category% and the %gemstone_slug% is assumed to be the %product_slug%. I'm having trouble thinking of a way around this, but URL rewriting is pretty new to me. Anyone have any thoughts?

As a bonus, another problem with the product permalinks is that their attachment pages (e.g. example.com/shop/%product_category%/%product_slug%/%attachment%) all 404 as well. For reference, I have opened a bug ticket for the attachment page issue on the WooCommerce github.

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Ok, the solution here turned out to be setting the correct priority on the add_action hook. Since we're all hooking into init to register our post types per the Codex, the priority will determine which register_post_type function gets called first and, by extension, the order of the generated rewrite rules.

So, I needed my "gemstone" rewrite rules to be checked before the "product" rewrite rules, so if they match, the product rules won't even be checked. It's a bit annoying that I had to use a negative value for the priority argument to achieve this because WooCommerce uses a priority of 0 for their register post type action, but that's a minor issue.

I still don't know how best to make the attachment pages work (the bonus question from above), but that is probably best left to the core WooCommerce team.

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