Really Mushy Pears

 The chocolate is perfect for hiding brown pears.
Chocolate-Pear Bread Pudding
Makes one 9x5 inch loaf

8 ounces challah, cut into 1-inch cubes
3 tablespoons unsalted butter
1 cup plus 3 tablespoons light brown sugar
2 Warren pears, peeled, cored, and sliced ¼-inch thick (or whatever you have)
1 ½ teaspoons ground cinnamon
2 tablespoons plus 1 teaspoon juice or juice syrup (my substitution for brandy,  also can use 1 3/4 t. brandy extract plus 5 1/4 t. water)
1/3 cup cocoa powder
1/8 teaspoon fine sea salt
4 ounces bittersweet chocolate, chopped
2 cups half-and-half
3 large eggs, at room temperature
3 large egg yolks, at room temperature
1 teaspoon vanilla extract
Whipped crème fraiche or creme, for serving

  1. Preheat the oven to 350°F. Spread the challah on a large baking sheet and toast until golden, about 10 minutes. 
  2. In a large skillet over medium-high heat, melt 3 tablespoons butter with 3 tablespoons sugar. Add the pears and ½ teaspoon cinnamon. Cook, tossing occasionally, until the pears are almost tender (but not mushy) and the liquid has reduced to a thick, syrupy glaze, 5 to 7 minutes. Sprinkle the pears with 1 teaspoon brandy. 
  3. In a small bowl, whisk together the remaining 1 cup sugar, cocoa, remaining 1 teaspoon cinnamon, and salt. Place the chopped chocolate in a bowl. In a small saucepan, bring the half-and-half to a simmer. Whisk in the cocoa mixture until smooth. Pour the hot liquid over the chopped chocolate and stir until chocolate melts completely. In a medium bowl, lightly beat the eggs and yolks. Slowly beat in the hot chocolate mixture until combined. Whisk in remaining 2 tablespoons brandy and vanilla. 
  4. Line a 9 by 5-inch loaf pan with parchment, allowing enough paper to hang over the edges of the pan. Spray with baking spray or coat lightly with butter. Layer half the pears into the bottom of the pan, top with half the bread. Repeat. Pour the chocolate custard over the mixture. Press down lightly with the back of a spoon so that the bread absorbs the custard. Let stand for 1 hour, pressing the bread down occasionally to soak up more of the liquid. 
  5. Preheat the oven to 325°F. Place the loaf pan inside a large, deep roasting pan. Fill the roasting pan with enough hot water to come halfway up the sides of the loaf pan. Bake until pudding is firm to the touch and the bread is golden, 45 minutes to 1 hour. Let cool completely in the pan on a wire rack. Chill pudding for at least 4 hours, until very firm. Grasp the parchment by the overhanging edges and lift out the pudding. Slice and serve, topped with whipped crème fraiche or creme.

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