I won a war against one of the AI, and it was supposed to become my vassal. After I accepted the peace offer, the AI didn't actually become my vassal though. There have been a couple crisis where I was able to demand that the AI give me an outpost, and I would make the demand then the AI would accept it but I never actually get the outpost they agreed to give me.
When you demanded the outpost, was it when there were 2 of the same listed, and one was cheaper? The cheaper one is the territory attached to a city, and the main one (80 points I believe), is the actual city. So if it lists:
San Lorenzo 80
La Venta 80
La Venta 42
If you choose San Lorenzo, the La Venta 42 will highlight if the territory is next to San Lorenzo. You won't get La Venta the city, though. This allows you to reattach the territory to San Lorenzo
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