📖 Instructions

1. Preheat your oven to 350°F (175°C). Grease a 9x13 inch baking dish. This is super important; you don't want your pudding sticking to the dish!
2. In a large bowl, mash the cooked pumpkin until smooth. I find a potato masher works best for this, but you could use a fork if you're feeling old-school.
3. In a separate bowl, whisk together the eggs, milk, brown sugar, vanilla extract, cinnamon, nutmeg, and salt. Don't over-whisk; we don't want any overly frothy mixture. Just a nice gentle mix is all we need.
4. Gently fold the pumpkin puree into the wet ingredients. Mix until just combined. We don't want to overmix and make it tough. Don't worry about a few little lumps; it will all come together nicely in the oven.
5. Cut the bread into 1-inch cubes. I prefer challah but really, any bread that's a bit sturdy will do. Day-old bread is ideal. If you use fresh bread, just make sure you don't over-soak it in the custard.
6. In the greased baking dish, layer half of the bread cubes, then pour half of the pumpkin mixture over the bread. Repeat layers with the remaining bread and pumpkin mixture. Make sure all the bread is nicely soaked, otherwise it will be dry. If you have any bread that isn't soaked through, add a bit more of the mixture.
7. Let the bread pudding sit for at least 15 minutes to allow the bread to absorb the custard. This step is key to a moist and flavorful pudding. You can do this while you prepare the caramel sauce.
8. For the caramel sauce: In a medium saucepan over medium heat, combine the sugar and water. Do not stir! Let it melt until golden brown, swirling the pan occasionally. Be careful, caramel is HOT and can burn your skin easily. Once golden brown, carefully remove it from the heat and slowly whisk in the heavy cream. It will bubble up quite a bit; be ready for it!
9. Pour the caramel sauce over the bread pudding mixture in the baking dish. Evenly distribute it to cover the top. I kinda like letting some of the bread peek out, but that's just me.
10. Bake for 45-50 minutes, or until the pudding is set and golden brown on top and a knife inserted into the center comes out clean. If the top is getting too brown, cover it loosely with foil for the last 15-20 minutes of baking.
11. Let the bread pudding cool slightly before serving. Warm bread pudding is wonderful, but it is also delicious at room temperature! Let it cool for at least 10-15 minutes. Patience, my friend. Patience.
12. Slice and serve. Enjoy your delicious homemade pumpkin squash bread pudding with caramel sauce!