Mexican Chocolate Bread Pudding (with Orange-Scented Whipped Cream)

Happy holidays everyone (all 5 of you)!  I've been too busy moping (the boyfriend is out of town) to even doodle, let alone cook (except truffles, but you can't have that recipe).  But it's Christmas Eve, so my mom made her famous enchiladas.  I quickly volunteered for a Mexican-inspired dessert.  IMPORTANT:  you need to start this recipe a day in advance!

That is the Table Moose.  He is present for every holiday,
dressed for the occasion, as the centerpiece.

Pudding:
1 loaf challah bread (check Whole Foods in areas with high goyum populations)
2 cups heavy cream
1 1/2 cups milk
8 oz semi-sweet chocolate chips, plus 1/4 cup (optional)
2 eggs
2 egg yolks
1 1/4 cups sugar
1 tsp cinnamon
    pinch salt
    pinch cayenne

Whipped Cream:
2 cups heavy cream
4 Tbsp. powdered sugar (granulated should work in a pinch)
2 tsp. vanilla extract
4 tsp. orange extract
    juice of half an orange

Garnish:
white decorating sugar
zest of one orange

1. Chop the challah into 1" cubes.  Either let it sit out on a cookie sheet for 24 hours OR toast at 325 F for about 20 minutes, until pretty hard.  If toasting, make sure the bread has a chance to cool completely.
2. The night before:  heat cream and milk over medium high until simmering.  Remove from heat.  Add 8 oz. chocolate and let sit 1-2 minutes.  Whisk together.
3. Meanwhile, beat together eggs, yolks, sugar, cinnamon, salt, and cayenne.  While the egg mixture beats, add the cream mixture one ladle-full at a time (you should do about 4 ladles or so, until the eggs are room temperature or warmer.  Then just pour in the rest).  Beat together until incorporated.  Refrigerate the custard overnight.
4. The morning of:  Grease two 9" round cake pans.  Distribute the challah cubes evenly in the cake pans.  Pour the custard over the challah cubes (again, distribute evenly).  Split the 1/4 cup chocolate chips evenly.  Toss the challah, custard, and chocolate chips until evenly coated.
5. Cover the pans with plastic wrap and press down to pack the cubes tightly together.  Place in the refrigerator.  Periodically, remove the pans, stir the cubes, then pack them down again (maybe 3 times throughout the day).
6. Preheat oven to 325 F.
7. Remove plastic wrap (making sure the cubes are firmly packed first).  Bake for about an hour.  Pudding is done when you meet resistance when you press firmly in the center.
8. While pudding is cooking, prepare the zest: zest the orange.  Spread the zest out on foil, and cook at about 100 F in the toaster oven until dry, about 10-20 minutes.  If you don't have a toaster oven, the zest can probably be left out to dry, starting the night before; alternatively, prepare the zest before the pudding bakes.
9. Pour the 2 cups whipping cream into a mixing bowl.  Refrigerate the bowl (filled with cream) and the beaters.
10. Remove pudding from the oven and allow it to cool in the pan on a wire rack, about 15 minutes.
11. Meanwhile, prepare the whipped cream: beat the cream until it begins to thicken.  Add the sugar, extracts, and juice, and continue to beat until firm peaks form.  If you can scoop it and it holds its shape, it's done.
12. Serve bread pudding with a generous dollop of whipped cream, sprinkled lightly with the decorative sugar (for sparkle) and the dry orange zest.

Baked pudding, pre-serving.