Custom Sidebar not showing Custom Post Type Categories

I'm running a directory theme that creates custom post type called "Places" which are categorized.

Currently, clicking on a "places" category results in a "places" page with sidebar that is the same across all categories.

I'd like to create custom sidebars for the different "Places" categories - but the options in Custom Sidebars Pro aren't showing the different categories - only "uncategorized" - which I suspect means it's drawing only from the standard post type (even though it seems to show the custom types).

Any ideas? Here's a video clip showing the issue.