I asked this question about 4 years ago and thought I'd ask it again to see what current "conditions" are. Has anyone had problems, or known anyone who did, boarding with a small, soft-sided, collapsible, lunch sack/cooler? Ours are maybe 9" long, 6" wide and 6" tall with shoulder straps. Just wondered if they'd try to count a lunch tote as a third item. We have taken these lunch sacks with us many times, but this February leaving Kauai for Honolulu we were told by the gate agent that we needed to stuff the sacks into our luggage because the flight attendants wouldn't let us on with three items. I muttered to my husband to just keep walking and we'd deal with the sacks at the door to the plane if someone called us on it, and they didn't. We are about to head off to Chicago on American this weekend, lunch sacks in hand. Because I'm a worrywort and we are pretty good about travelling light, there will no doubt be room to spare in our luggage if need be.