I send my luggage through first as I use it as the support for the workbag. I plunk it on the floor, pull up the handle then feed the workbag (there is a zippered opening for that purpose) over the handle and then pull it all away... I keep the workbag (which has a pocket with all of my personal "stuff") last, as I want to keep my eyes on it as long as possible! Sometimes you get held up walking through the metal detector. When that happens I never take my eyes off my bags, and if they move out of sight I alert the TSA worker to that fact. They are very quick to respond to that, as they can't (won't?) take responsibility for things going missing during the process. All in all the key for me is to be totally organized, and have a routine.