Jail Storage Permissions Difficulties

Here is the setup I am trying to create: I want a single location where files are downloaded to by both SABnzbd and Transmission, and I want to be able to browse to that location via a CIFS share.

Here is my setup that seems like it should work, but does not.

I have my username, call it WhirlwindMonk, setup. I have a user and a group called transmission, both id 921. I have a user and a group called media, both id 816. transmission also has media added as an Auxiliary group.

I have a dataset...

Jail Storage Permissions Difficulties