Hello: If wanting to have outlook automatically delete emails from the deleted folder, please do the following.
Alt-f for the backstage 2. up arrow and press enter on options 3. Press the letter "A" for advance 4. Press your tab key until you hear empty deleted items folder when exiting outlook and if the box is unchecked, check it with the spacebar. 5. Tab to the ok button and press spacebar. For answers to frequently asked questions about this list visit: http://www.jaws-users.com/help/