After changing the nginx config twice to include new folders, I fixed the default path of assets to point to a common folder.
Paperclip::Attachment.default_options[:path] = ‘uploads/:class/:attachment/:id/:style_:basename.:extension’
I was toying with setting expiry headers for page cached content to 12 hours using similar nginx directives. (expires 12h;) However, the first request 404s since nginx breaks before the mongrel has generated the content. A simple post deploy recipe to touch all cached pages works but feels dirty. Is there more nginx trickery for this situation?