Private Messaging Plugin no longer showing ability to attach

We purchased a membership & the plugin private messages. At first, we could attach pdfs (etc) - but now the option is gone (all within a few minutes of testing). We do have it enabled & the roles are applied: http://www.screencast.com/t/utuQPyeo6 , http://www.screencast.com/t/K6jseq63nN9