adapted from Cooks Country
Serves: 16
Position oven rack to the middle
Preheat oven: 350°
Plan ahead: The cake must be baked in a water bath so you will need to check the size of your bundt and your roasting pan.
It must also chill for 8 hours after baking.
Cake
1/2 cup caramel sauce
1/2 cup plus 2 Tbsp. all-purpose flour
1/3 cup cocoa powder
1/2 tsp baking soda
1/8 tsp salt
4-ounces bittersweet chocolate, chopped
6 Tbsp. unsalted butter, melted
1/2 cup buttermilk
1/2 cup sugar
2 eggs
1 tsp vanilla
Flan
2 (14-ounce) cans sweetened condensed milk
2 1/2 cups whole milk
6 ounces cream cheese, room temperature
6 eggs
4 egg yolks
1 tap vanilla extract
Cake: Thoroughly grease a 12-cup bundt pan. Microwave caramel until easily pourable, about 30 seconds. Pour caramel sauce into the bottom of the bundt pan. In a medium bowl, combine flour, cocoa, baking soda, and salt. Set aside.
Place chocolate and butter in a microwave safe bowl, heat until melted, 2 minutes at 50% power. Whisk buttermilk, sugar, eggs, and vanilla into chocolate until incorporated. Add flour mixture and stir until combined. Pour batter over caramel.
Flan: Add sweetened condensed milk. milk, cream cheese, eggs, egg yolks, and vanilla to a blender, Blend until very smooth, about one minute. Slowly pour flan mixture over cake batter.
Place a large roasting pan on the oven rack. Place the bundt pan in the roasting pan. Pour boiling water halfway up the sides of the bundt pan. Bake for 75 to 90 minutes, or when a toothpick comes out clean. (Test at 75 minutes.) The flan should register 180°.
Transfer to a wire rack and cool to room temperature, about 2 hours. Refrigerator and chill for at least 8 hours to allow the flan to set.
To unmold, place the bottom of the cake pan in hot water for 1 minute. Place a completely flat cake plate over the bundt pan and flip over. Slowly remove bundt pan allowing the caramel to drizzle over the top of the cake. Serve with additional caramel sauce drizzled over the top of each piece.