On Oct. 20, 2011, Secretary of State Hillary Clinton was aboard a C-17 Globemaster military plane bound for Libya. While waiting for takeoff, Clinton—wearing a pair of dark sunglasses—began pecking at her smartphone, her face a mask of determination. Alert to an iconic moment, a Reuters photographer clicked his shutter. National media picked up the photo, which inspired a satiric Tumblr called Texts From Hillary. Years later, it became a flashpoint in an investigation that revealed the Secretary of State was using a private email address for government business. That controversy, as we know, helped to steer an election.