dark chocolate caramel bread pudding

I love my mom. For too many reasons to list, one of them being that she so totally understands me. The other day she came home with a giant loaf of challah bread, and went, "I found this in the clearance bin. I figured you could bake something with it!" How did she know I have been wanting to make challah bread pudding for ever? I don't know, y'all. Sometimes I think she can read minds. 

For those of us who didn't know before, challah is different from regular bread because it's made with numerous egg yolks and lots of butter, making it super rich and soft. Therefore perfect for slathering with more sugary goodness, right? I have already made tiramisu bread pudding, and almond chocolate chip bread pudding, so I figured it was time for something new. Still including chocolate, of course! I topped this particular pan of deliciousness with dark chocolate chunks, pecans, and homemade microwave caramel sauce {which I found on Gimme Some Oven's blog. It's kinda sorta lifechanging}. It was basically the best thing ever. I'm pretty sure ooey gooey was coined after somebody ate homemade bread pudding slathered in chocolate and caramel. But for real. Make this!

Dark Chocolate Caramel Bread Pudding
Caramel recipe from Gimme Some Oven
Yields: one 9x13 pan

1 loaf challah bread
2 cups milk
3 eggs
½ cup brown sugar
1 teaspoon vanilla extract
1 cup dark chocolate chunks
1 cup pecan halves, chopped
½ cup white granulated sugar
1 tablespoon light corn syrup
1 tablespoon water
squeeze of lemon juice
¼ cup heavy cream, heated
¼ teaspoon vanilla extract
½ tablespoon unsalted butter, plus more for greasing

Preheat the oven to 350F, and butter a 9x13 baking dish. Slice and dice your challah bread in 1" cubes, more or less, removing most of the bread "skin". In a large bowl, whisk together the milk, eggs, brown sugar, and 1 teaspoon vanilla. Add in the bread cubes, mix everything together, and set aside while you make the caramel. In a microwave-safe measuring cup, combine the white sugar, corn syrup, water, and lemon juice. Microwave on high 2-3 minutes, until the mixture turns a pale golden. Watch it very carefully, because it can burn very quickly! Not that I'd know anything about that... Remove from the microwave, and let the sugar mixture rest at room temperature 3-5 minutes, until it turns a deep amber color. Add in about a tablespoon of the heated cream, and whisk vigorously. The mixture will bubble like crazy! Keep whisking and adding in the cream until all has been added. Whisk in the ¼ teaspoon vanilla and ½ tablespoon of butter, and set aside while you finish the bread pudding. Pour about half of your soggy bread cube mixture into your prepared buttered dish, and top with half of the chocolate chunks, pecan chunks, and caramel sauce. Top with remaining bread mixture, and top that with the remaining toppings. You can keep some caramel sauce for serving! Bake in your 350F oven for 30-40 minutes, until a toothpick inserted in the center comes out with a few moist bread crumbs. Let cool slightly, and serve warm with additional caramel sauce. Enjoy!