The Flying Kipper is the nineteenth episode ever made in Season 1.
One night in winter, after his day's work is done, Henry is told by his driver that they will be leaving early in the morning to pull "The Flying Kipper", a train from the quay that carries fish from the harbour to the mainland. The driver tells Henry that his special coal is working so well that if he pulls the Flying Kipper nicely, the Fat Controller will let him pull the express, a thought that makes Henry very happy.
Early next morning, Henry arrives at the quay ready to pick up the Flying Kipper. Everything goes very smoothly and Henry leaves the harbour without a hitch. After getting the vans to come along quickly and quietly, Henry quickly begins to enjoy his journey marveling at the countryside as the sun rises.
Soon Henry comes to a yellow signal indicating caution. Henry's driver initially prepares to stop, until he sees the signal is down meaning that the line ahead is clear. With that, the driver allows Henry to continue at full speed. What the driver doesn't know, however, is that the points from the main line to a siding had been frozen, and the signal, which should have been set at "danger", had been forced down by snow.
In the siding is a goods train which had been pulled in to let the Flying Kipper pass and the engine's crew is enjoying cocoa in the brakevan. However the crew notices that is nearly time for Henry to pass by, so the crew leaves to return to their engine. Their escape comes just in time, as Henry comes flying down the siding at full speed and, unable to stop, crashes straight into the train causing a massive wreck which completely destroys the brakevan and causes Henry to derail.
A few hours later, the clean-up effort is underway. Henry's driver and fireman had jumped clear before the crash, but Henry is left on his side dazed. The Fat Controller comes to talk to Henry and kindly reassures him that the accident was not his fault, but was caused by the weather. He then tells Henry that he is going to be sent to Crewe, an excellent place for sick engines. As well as repairing him, they will also give him a brand new shape and a larger firebox. As a result, Henry will feel much better and will not need special coal anymore.
A few weeks later, Henry returns from Crewe. Although he enjoyed his time there, he is happy to return to the Island of Sodor. A lot of people wait at the station to welcome him home and see him in his new shape. When he rides through, he looks so splendid and strong that the crowd gives him three cheers much to Henry's gratitude. A lot of children are now often late for school as they want to wait to see Henry ride by and often see him pulling the express. He is able pull it so well that Gordon feels jealous, but that is another story.
- Henry's eyes jitter in the close-up of him in the shed.