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Valentine's Day Box of Chocolates Cut Out Cookies

These delicious brownie chocolate cut out cookies are topped with a soft vanilla buttercream frosting and decorated like a box of chocolates. Gift your loved ones the perfect Valentine sugar cookie!
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Course: Dessert
Cuisine: American
Keyword: Chocolate Cut Out Cookies, Cut Out Cookies, Sugar Cookies, Valentine Sugar Cookies
Prep Time: 1 hour
Cook Time: 10 minutes
Decorating Time: 4 hours
Total Time: 5 hours 10 minutes
Servings: 18 cookies, depending on the size of your cookie cutter

Equipment

  • Stand Mixer with Paddle Attachment
  • Mixing Bowl
  • Rolling Pin
  • Heart cookie cutter
  • Cookie Sheet
  • Icing Bags
  • Couplers
  • Decorating Tips
  • Palette Knife

Ingredients

Chocolate Fudge Cut Out Sugar Cookies

  • 3 cups all purpose flour
  • 1 package Chocolate Fudge instant pudding mix 3.9 ounce package
  • 1/2 cup cocoa powder
  • 1 cup cold salted butter
  • 3/4 cup granulated sugar
  • 1/4 cup dark brown sugar packed
  • 1 egg
  • 1 tsp vanilla extract
  • 1-3 tbsp canola oil, or preferred light tasting oil see instructions

Crusting Vanilla Buttercream for Sugar Cookie Decorating

  • 1 cup unsalted butter room temperature
  • 4 cups powdered sugar
  • 1 tbsp vanilla extract
  • 1-3 tbsp whole milk, half & half, cream, or water
  • brown, orange, and red gel food dye see section 2 for color mixing notes
  • Valentine's Day sprinkles

Instructions

Chocolate Fudge Cut Out Cookies

  • Preheat your oven to 350 degrees Fahrenheit and take out the cup of unsalted butter to begin to come to room temperature. The unsalted room temperature butter is for the buttercream.
  • In a large mixing bowl, mix your flour, cocoa powder, and Chocolate Fudge pudding mix together. When measuring the flour, make sure to scoop up the flour with a spoon and add it to your measuring cup, one spoonful at a time. This helps obtain the correct amount of flour without needing to weigh it. Once you have a cup, level it out by running a knife across the top of the measuring cup.
  • In your electric mixer, combine the white and brown sugars with the butter using the paddle attachment until they are creamed together.
  • Add in your egg, 1 tablespoon canola oil, and vanilla extract and mix to combine.
  • Slowly add in the flour, cocoa powder, and pudding mixture to the wet ingredients and combine. The combined mixture will be crumbly but still form a ball if picked up and molded into a ball. If it is too crumbly, add in another tablespoon of canola oil.
  • On a floured surface, roll out the dough to about a 1/4 of an inch thick & cut out your cookies. A great tip is to flour your rolling pin. Transfer the cut out cookies to a baking sheet lined with a  silicone mat or parchment paper.
  • Bake for 9-10 minutes and let cool on the baking sheet. The dough will be done when the center of the dough doesn’t look wet. It is better to undercook the cookies than to overcook them, as it will be difficult to watch for burns with these dark sugar cookies.
  • Optional but highly suggested: Place the cooled cookies into an airtight container and freeze them overnight. Remove the container from the freezer 1 hour before decorating for soft brownie chocolate cut out cookies.

Crusting Buttercream

  • In a stand mixer with the paddle attachment, cream the unsalted room temperature butter until light and fluffy, about five minutes on high.
  • Add in the powdered sugar, vanilla extract, and one tablespoon of milk. Cover the mixer with a paper towel or clean tea towel and mix on low until combined. If the frosting is too thick (thicker than smooth peanut butter) add more milk, up to two more tablespoons.
  • Follow the instructions in Part 2 for how to divide up the frosting, dye it, and prepare the icing bags.

Decorating the Valentine Sugar Cookies

  • Follow the instructions in Part 3 for decorating the sugar cookies.