Flag Flying is a magazine story.
It is Flag Flying Day on Sodor. Everywhere Oliver puffs he sees flags, including the Sodor Yacht Club and Callan Castle. At the main station, he tells Emily what he saw. Then the Fat Controller speaks to some of the engines. He tells them that they will be very busy taking tourist specials all over the Island. Oliver is worried that with so many trains, the passengers will get confused. Before Emily sets off on her school run, she speaks to the Fat Controller, who organises a painting competition at the school. The headmaster selects the best paintings and the Fat Controller sends them off to a flag maker.
Some time later, the tourist's special trains are waiting at the station. To avoid confusion, each engine has flags attached to their funnels. Henry's flag indicates that he is going to the forest, Oliver's the pier, and Emily's the school run. Oliver is delighted with the flags that the school children designed.
- In one illustration, Henry is missing the red lining on his firebox and the yellow lining around his windows.