Sweet Potato Pie Bread Pudding with Bourbon-Pecan Hard Sauce

ACTIVE: 40 MIN TOTAL TIME: 1 HR 45 MIN SERVINGS: 2 "pies" or 16 servings

1              stick plus 3 tablespoons unsalted butter, softened, plus melted butter for brushing
1              pound challah bread, cut into 1-inch cubes
1              2-pound butternut squash
1-1/4       cups sugar, plus more for sprinkling
4              large eggs
3              cups whole milk
1              14-ounce can sweet potato pureed in blender
1-1/2       teaspoons ground cinnamon
1/2           teaspoon freshly grated nutmeg
1/4           teaspoon ground cloves
1/2           teaspoon kosher salt
2              cups confectioners’ sugar
2              tablespoons bourbon
1/2           cup chopped toasted pecans

1 .      Preheat the oven to 375°. Butter two 9-inch, deep-dish glass or ceramic pie plates. Spread the challah on a large baking sheet and toast for about 5 minutes, until lightly golden.
2 .      Cut the neck from the butternut squash. Peel it and cut it lengthwise into two 3/4-inch-thick slabs. Very thinly slice the slabs into long, thin strips on a mandoline. Peel, seed and cut all of the remaining squash into 1/2-inch dice.
3 .      In a very large nonstick skillet, melt 3 tablespoons of the butter. Add the diced squash and cook over high heat until lightly browned in spots, about 3 minutes. Add 1/4 cup of the sugar and cook, stirring occasionally, until just tender and glossy, about 3 minutes longer. Let cool.
4 .      In a large bowl, whisk the remaining 1 cup of sugar with the eggs, milk, sweet potato, cinnamon, nutmeg, cloves and salt. Add the sautéed squash and the challah and gently toss to combine. Spoon the mixture into the buttered pie plates and top each with a loose lattice pattern of the squash strips. Brush the strips with butter and sprinkle with sugar. Cover with parchment and bake for 30 minutes. Uncover and bake for 30 minutes longer, until the tops are golden and the puddings are set. Let the puddings rest for 15 minutes.
5 .     In a bowl, whisk the remaining butter with the confectioners’ sugar, bourbon and pecans. Serve the pudding with the sauce.

Make ahead :
The bread puddings can be covered and refrigerated overnight. Rewarm at 300° for about 15 minutes before serving.

Suggested Pairing Smooth, dried cherry–scented tawny port: Fonseca 10-Year.

TIP :
These creamy sweet potato bread puddings are baked in pie dishes so they’re like a hybrid dessert; the lattice top is actually made of strips of butternut squash.