If I have a post in multiple categories, what defines what category shows up in the URL? Assuming I have permalinks setup as /%category%/%postname% is it the ID or the name?
What Defines What Category A Post Picks (if in multiple)
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WordPress always use the category with lowest ID. You can use plugins such as the Hikari Category Permalink plugin to change that however.
http://wordpress.org/extend/plugins/hikari-category-permalink/