* CultClassic -- ''The Settlers II'', in particular its idiosyncratic infrastructure (segmented roads with each carrier relaying wares along their segment), attracted such a cult that it was remade in 3D on its tenth anniversary and also inspired the open-source game ''Widelands''. Ironically, this iconic mechanism was likely influenced by early technical constraints, as it required far less pathfinding work for the computer compared to carriers walking around freely.
* GameBreaker -- Catapults in ''The Settlers II'' didn't break peace agreements, so you could just use them to bomb through most of the opposition base.
* ThatOneLevel -- Campaign level 6: The first level where there is no initial peace treaty with your more powerful, aggressive rivals.
* TheyChangedItNowItSucks -- Every game after the second, but particularly ''Heritage of Kings'' and ''[[VideoGame/TheSettlersRiseOfAnEmpire Rise of an Empire]]''.
* UnfortunateImplications -- In ''The Settlers II'' you could play as Romans, Africans, Vikings, or Japanese but your peasants remained Caucasian regardless, implying a universal use of white people as slaves.