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Position rack in upper third of oven. Preheat to 350°F.
Brush all sides of 6 apple halves with 1 tablespoon oil; place cut-side down on a large rimmed baking sheet. Bake until soft but not mushy, 15 to 20 minutes. Remove from oven and turn broiler to high.
Meanwhile, stir ¼ cup brown sugar, 2 tablespoons butter, ¼ cup pecans and ¾ teaspoon cinnamon together in a small bowl.
Using the bottom of a Mason jar or other sturdy glass, flatten each apple half. Divide the cinnamon-sugar mixture among the apples. Broil until the pecans are browned, 1 to 2 minutes. Serve warm.