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Chocolate Rum Whoopies with Dulce de Leche Filling

These Chocolate Rum Whoopies filled with Dulce de Leche, the sweet caramel filling were perfect for the Holiday Cookie Swap in NYC organized by Bloggers Without Borders for WhyHunger. I have baked these chocolate cookies before on other occasions. They are filled with the robust, chocolatey flavors and as a treat, a dash of rum goes into the batter. The decadent Dulce de Leche filling is easy to make either stove top or in a slow cooker like I did. This rich caramel filling from a can of condensed milk was inspired by the recipe blog 80Breakfasts, of my dear friend, Manila-based food blogger @80Breakfasts. This original cookie recipe of my sister, Isabel Besa Morales M.S.R.D., makes 36 pieces or 18 pairs of chocolate sandwiches.
Prep Time1 day
Cook Time10 minutes
Resting Time30 minutes
Total Time1 day 40 minutes
Course: Dessert, Snacks
Cuisine: American, Asian, Filipino
Keyword: Chocolate Rum Whoopies
Servings: 4 people
Calories: 1181kcal
Author: Asian in America

Equipment

  • Large Cookie Sheets

Ingredients

  • 3 cups All Purpose Flour
  • 2 cups granulated sugar
  • 1 1/2 cups cocoa powder
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 4 whole eggs
  • 3/4 cup vegetable oil
  • 2 teaspoons vanilla extract
  • 2 Tablespoons rum
  • 1 can (14 oz.) sweetened condensed milk

Instructions

  • To make Dulce de Leche: remove paper labels from the can of condensed milk. Fill a large pot with water, enough to cover the can. Let the water boil, then simmer over medium heat to cook the condensed milk inside the can. Cook for 3 hours. If using a Slow Cooker like I did, cook the can of condensed milk on HIGH settings for 4 hours, with water covering the can. After cooking time, leave the can submerged in the water and let it get to room temperature. Then refrigerate can of caramel condensed milk overnight and set aside till ready to spread as cookie filling.
  • To bake the cookies: Preheat the oven to 350 F degrees to bake the cookies.
  • Line baking sheets with parchment paper.
  • In a large bowl, place all the ingredients together : Flour, sugar, cocoa powder, baking powder, salt, eggs, corn oil, vanilla and rum. Using a stand mixer, mix all the ingredients till well blended. Batter will get thick and easier to handle by hand.
  • Shape the cookie dough into round chocolate balls about 2 inches in diameter.  Arrange the cookie dough balls on the cookie sheet, about 2 inches apart.
  • Bake at 350 F degrees for 9 to 10 minutes. When cookies are done, cool on a rack for at least 30 minutes.
  • Make sure cookies are thoroughly cooled before placing the filling.
  • To assemble chocolate cookies : Take the bottom cookie, spread a tablespoon of the caramel dulce de leche (from the cooked condensed milk). Place another cookie on top of the filling to form a chocolate sandwich. Press cookies together. Wrap in plastic and freeze cookies till ready to serve.

Nutrition

Serving: 1g | Calories: 1181kcal | Carbohydrates: 191g | Protein: 16g | Fat: 46g | Saturated Fat: 36g | Cholesterol: 4mg | Sodium: 304mg | Potassium: 743mg | Fiber: 13g | Sugar: 101g | Calcium: 120mg | Iron: 9mg