Continuity mistake: Despite Henry's issue from "Coal" in Season 1 being resolved after the crash in "The Flying Kipper", also in Season 1, Henry needed special coal again from "Thomas and the Magic Railroad" until Season 16.
Continuity mistake: Bulgy was converted into a vegetable stand in "Bulgy Rides Again." But from "Excellent Emily" onward, he is a passenger bus again.
Continuity mistake: Throughout Season 4, Henry is painted in two different shades of green.
Revealing mistake: When Thomas collects Rocky, the points are set against him. This also happens when Percy enters the siding.
Answer: Butch the breakdown truck must have pulled Gordon's tender all the way up the rails so the breakdown train can reach it and also Butch helped to get Gordon close to the winch.