Not sure about the files in Outlook. The Norton Protected Recycle Bin, merely stores deleted files for a time, in case you decide that you did not want to delete a particular file after all. You can safely empty it as often as you want, so long as you are sure that you no longer want any files that it contains. In any case once it reaches a certain capacity, the first files saved in there start to delete themselves, saving only the latest deletions. It will not contain any important files UNLESS you have deleted them, and put them in there.