1 1-lb. loaf challah, cut into 1-inch cubes
8 T. butter, melted
½ cup orange marmalade
1 c. semisweet chocolate chips
1 teaspoon grated orange zest
2 c. half and half
1 c. sugar
5 large eggs
2 large egg yolks
4 t. vanilla extract
Pinch salt
Preheat oven to 350°F. Butter a 1.5 quart casserole dish, or 6-8 individual ramekins. Spread marmalade onto the bottom of the prepared dish. (If using ramekins, place 1 tablespoon of marmalade in each dish, spreading to cover the bottoms.)
Place bread in large bowl; pour 8 tablespoons melted butter over bread and toss to coat. Add chocolate chips and zest, and toss to combine. Transfer mixture to casserole dish.
Whisk together half and half, sugar, eggs, yolks, vanilla, and salt in large bowl. Pour over bread cubes in dish. Let stand 30 minutes, occasionally pressing bread cubes into custard. (At this point it can be covered and refrigerated overnight.) Bake bread pudding until puffed, brown, and set in center, about 1 hour for casserole, 40-45 minutes for ramekins.
Dust with powdered sugar, if desired. Serve warm with Cinnamon-Rum Sauce.
Cinnamon Rum Sauce
1 cup butter
1 cup dark brown sugar
½ t. ground cinnamon
¼ teaspoon salt
¼ cup dark rum
Melt unsalted butter in heavy medium saucepan over medium-low heat. Add dark brown sugar, ground cinnamon, and salt, and whisk until sugar is dissolved and mixture is bubbling and smooth, about 4 minutes. Remove from heat. Whisk in dark rum and vanilla extract. Serve warm.
(Cinnamon-Rum Sauce can be prepared 2 days ahead, covered, and refrigerated, and warmed just before serving. It is excellent over ice cream, apple pie, apple dumplings, you name it!)