Bread Pudding
1 (1 pound) loaf challah or firm-textured French bread, cut into 1-1/2 inch cubs (4-1/2 cups)
1-1/2 Tablespoons unsalted butter, softened
1-1/2 cups heavy cream
1-1/2 cups whole milk
1 cup canned unseasoned pumpkin puree
1-1/2 teaspoon ground cinnamon
Heaping 1/4 teaspoon ground nutmeg
1/8 teaspoon ground allspice
2 extra-large eggs
2 extra-large egg yolks (in addition to the two eggs)
1/3 cup packed light brown sugar
1-1/2 teaspoons pure vanilla extract
1/4 teaspoon salt 

Preheat the oven to 350° F with a rack at the center position. Place the bread cubes on a rimmed baking pan and bake for 10 to 15 minutes to dry them out.  Use 1/2 tablespoons of the butter to coat the inside of the insert of the slow cooker.  Press the bread cubes into the bottom; they should fit snugly, and the bottom should be thoroughly covered.  Turn the slow cook to HIGH and let it heat, uncovered, while you prepare the pudding. 

In a medium saucepan heat the cream and milk until the mixture is very hot and starts to bubble, do not let it boil.  Remove from the heat. Place the pumpkin puree, cinnamon, nutmeg, allspice, eggs and egg yolks, brown sugar, vanilla, and salt in a large mixing bowl.  Whisk them together well, and then slowly pour in the hot cream mixture, whisking constantly. 

Turn the slow cooker down to LOW.  Carefully pour the pumpkin and cream mixture over the bread and push the bread pieces down beneath the mixture to moisten them. (They will pop up again; that's okay.) Dot the top with the remaining 1 Tablespoon of softened butter.  Cover and cook for 3-1/2 hours on LOW, or until an instant-read thermometer inserted in the center registers 190° F and a small knife inserted in the center comes out clean.  Turn the slow cooker off and let the pudding rest, covered, for 30 minutes. 
 

Bourbon Caramel Sauce and Whipped Cream
2 cups granulated sugar
1 cup water
1 Tablespoon strained lemon juice
4 Tablespoons unsalted butter, at room temperature, cut into 4 pieces
1/2 cups heavy cream, well chilled
1/3 cup bourbon
1 Tablespoon pure vanilla extract 

2 cups heavy cream, whipped with 1/2 cup sugar and 1 teaspoon vanilla

While the pudding is cooking, make the Bourbon Caramel Sauce.  Have all the ingredients ready before you begin.  

Place the sugar, water, and lemon juice in a large heavy saucepan.  (It must have at least a 2 quart capacity because the mixture will bubble vigorously when the cream and butter are added later and you don't want to get burned.) Bring the sugar mixture to a boil over medium-high heat; stir only until the sugar is dissolved and the syrup is clear.  Continue to boil, without stirring, until the mixture starts to turn an amber color, which may take as long as 15 to 20 minutes.  (Be careful, because it can burn very easily; if your eyes begin to sting it means it is starting to burn.) When the mixture has darkened to a rich caramel color, remove it from the heat and immediately stir in the butter, bit by bit, then 1/2 cup of the heavy cream and finally the bourbon and vanilla.  Cool to room temperature. 

While the sauce is cooling, beat the remaining 2 cups of cream with a whisk or electric mixer until it forms soft peaks. Add sugar and vanilla and mix.

To serve the pudding, scoop it into individual bowls, drizzle on some caramel sauce, then top with a dollop of whipped cream.