Permalinks Help

I’m having a heck of a time with permalinks. Seems like everything I change nothing matters. So I’m looking for some help.

So here’s my setup. I have a custom post type that I’ve setup for a portfolio style website. I also have a custom taxonomy to label these portfolio items. My portfolio section is just called “work”. And I have categories such as “print, web, multimedia”. That sort of thing.

I want my urls to be “/work/category_name/post_name/”. But no matter what I do I always get “/work/post_name/”.

What am I doing wrong and what can I do to fix this? Thanks!