"Embedded" Ruby environments like Vagrant and the Chef Development Kit have their own ideas for where things are supposed to be placed. Chef-DK in particular has its own preferred settings for PATH, GEM_ROOT, GEM_HOME, and GEM_PATH that at present don't play well with chruby's method of managing these variables.
Right now I work around this by creating some monster Bash aliases, chefdk and unchefdk, that switch between Chef-DK's and chruby's way of doing things. But it would be nice to be able to do it all through chruby (e.g. chruby chefdk).