This bread pudding was a request from a pregnant friend who was having very specific cravings! A homemade caramel sauce is the base for the custard, which is both flavored and thickened by pumpkin puree. And of course, lots of warm pumpkin pie spice make this the ultimate autumn dessert (pro tip: it also makes a great breakfast treat with coffee).
Preheat the oven to 325 degrees F. Spray a 9-by-13-inch baking dish with cooking spray.
Stir together the sugar and 3 tablespoons water in a medium saucepan until the consistency resembles wet sand. Brush down any sugar crystals from the sides of the pan with a wet pastry brush. Cook, undisturbed, over medium-high heat until the sugar melts and turns a dark amber, 8 to 11 minutes. Do not stir during this time but once it starts to turn caramel, you can swirl the pan to distribute the color.
While the caramel cooks, bring the heavy cream to a low simmer in a small saucepan. Once the caramel is dark amber, carefully whisk in the warm cream. The cream will bubble up. Add the butter and salt, whisk until smooth, then remove from the heat and set aside.
Whisk together the milk, eggs, yolks, pumpkin puree, brown sugar, pumpkin pie spice and vanilla extract in a large bowl. Carefully whisk in 1/3 of the warm caramel sauce until fully incorporated, then whisk in the remaining caramel sauce. Set aside.
Toss together the stale bread cubes and the pecans in the prepared baking dish, then arrange them in an even layer. Pour the caramel pumpkin custard over the top. Cover and let soak 30 minutes in the refrigerator, pushing down the bread occasionally to submerge it.
Bake until the custard has set and the top is a nice golden brown, 45 to 50 minutes. Remove from the oven and let cool slightly before serving with whipped cream or ice cream.
Cube the challah and let it sit out overnight to get stale. Alternatively, bake the cubes on a rimmed baking sheet in a 300-degree F oven until crisp and lightly toasted, about 20 minutes.
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