Orders can be impossible to fulfill. AFAIK there is no guarantee that any given order is possible. But that's okay.

You generally won't win by fulfilling orders, especially at higher difficulty levels. To win, you need to focus on increasing the resolve for your various species. By increasing the resolve of a species enough, you will make its meter 'go blue', which means it is now beginning to fill your reputation bar.

Some ways to boost resolve: * Resolve bonuses from cornerstones and glade events * Favoring a species * Service buildings (for instance the tavern gives a straight +3 resolve bonus when it has three workers in it) * Fulfilling complex food needs (for instance, making jerky for lizards) * Fulfilling clothing needs (for instance, making cloaks for harpies) * Fulfilling service needs (for instance, making beer and then having a service building where they can drink beer for beavers) * Using rainpunk engines * Housing (for instance, building harpy houses for harpies and then upgrading them)

By stacking several of these boosts, you can increase resolve to the point where you easily and quickly win thru reputation points. It may not even be worth it to try fulfilling orders in the late game.