* In "Island of Hope" in ''Tycoon 2's'' ''Second Century'' campaign, as in other maps the identities of train robbers is reflective of the map and the storyline. In this case, your trains will be robbed by "starving mob", since in the story food is very scarce. This leads to the BlackComedy of papers triumphantly declaring "Starving Mob Captured!" and celebrating it means no more train robberies.
* The [[ItsAWonderfulFailure game over message]] in the "Hell and High Water" mission, where the map is flooding. "So, how long can you tread water?"
* Certain maps in ''Tycoon 2'' do not allow any track to be built that is not connected to the rest of a company's network. On a map like China, this [[IdiotBall can lead]] to an AI player starting their company in a place like [[{{UsefulNotes/Taiwan}} Taiwan]], which does have two viable cities on the map but which is separated from the mainland [[DidntThinkThisThrough by a sizable stretch of open ocean]].[[note]]In the expansion Gold and Platinum Editions, you can build a bridge spanning ocean tiles to get to or from an island; the AI generally [[ArtificialStupidity never does this]], probably owing to the ShockinglyExpensiveBill.[[/note]]