
Preheat oven to 375°.
For the cups, prepare oranges by slicing ⅛-inch off the bottoms of each. Flip oranges over, cut off top third, and scoop out and juice the flesh; reserve juice for the filling.
Mash sweet potatoes, pineapple, reserved orange juice, softened butter, brown sugar, eggs, cinnamon, and salt. Fill cups with sweet potato mixture, then transfer to a baking sheet. Bake cups until tops begin to brown, about 45 minutes.
For the topping, toast pecans in a sauté pan over medium heat, 2 minutes. Add butter, brown sugar, corn syrup, and salt; cook until syrupy.
Off heat, stir in bourbon and vanilla. Return topping to medium heat for 1 minute, then spoon over baked orange cups and serve.