January 1, 2014
Oliver has been working at the docks since he arrived back from his overhaul. However, one day Sir Topham Hatt is at a shortage for engines, so he requests Oliver to pull the express coaches to help with the passenger rush. Oliver is in full doubt, especially due to Henry and Gordon's teasing. However, Duck reasures him that everything will be fine.
After more teasing from Henry and Gordon at the station, Oliver grows in confidence with encouragement from Thomas on his journey. Gordon teases yet again at Wellsworth, but after his driver reminds him of his bravery, Oliver finds he has the courage and strength to tackle Gordon's Hill after all.
At the next station Henry apologizes for being so rude and congratulates Oliver on his efforts. Furthermore, Sir Topham Hatt steps out of one of the carriages to say his thanks to Oliver and his triumph. At long last, Gordon gets his karma as he is destined to do the shunting in the yard as punishment for teasing, and Oliver due to recieve a fresh coat of paint.
- James (cameo)
- Percy (cameo)
- BoCo (cameo)
- Donald and Douglas (cameo; speaks in deleted scene)
- Stepney (cameo; speaks in deleted scene)
- Terrier55Stepney as Thomas
- Supermariokyle100 as Edward
- Ilovetrains323 as Henry and Sir Topham Hatt
- JD41796 as Duck and Gordon
- TheBlueE2 as Oliver
- The intro was created by 10leigh10.
- This was the first and only episode narrated by Mallardfan62.
- A mail-van is seen coupled to a ventilated van towards the beginning. This is an in-joke by the director between friends.
- Donald, Douglas and Stepney had scenes congratulating Oliver, But they were cut.
- This is the first episode of the series not to be based on a story from the real series.