Piping a swirl of cinnamon roll frosting by hand on top of the baked shortbread cookie filled with cinnamon roll filling being held by hand

Cinnamon Roll Shortbread Cookies


Piping a swirl of cinnamon roll frosting by hand on top of the baked shortbread cookie filled with cinnamon roll filling being held by hand

Cinnamon Roll Shortbread Cookies Recipe

These simple and quick cinnamon roll shortbread cookies are perfect for when you want a cinnamon roll but don’t have time to wait for dough to rise! They’re made with cinnamon roll filling and frosting, so you get all the flavors atop buttery, tender shortbread. All with pantry-friendly ingredients, they’re quick to prep and easy to make ahead.
Prep Time 30 minutes
Cook Time 15 minutes
Chill time 15 minutes

Equipment

  • Baking sheet
  • Parchment paper
  • heatproof bowl
  • Heavy Bottom saucepan
  • medium mixing bowl
  • Electric hand mixer or Stand mixer

Ingredients
  

Shortbread Cookie Ingredients:

  • 1/2 cup softened butter
  • 1/4 cup + 2 tablespoons superfine white sugar caster sugar
  • 1 1/2 teaspoons pure vanilla extract
  • 1 1/4 cups + 1 tablespoon all-purpose flour
  • 1/8 teaspoon salt

Cinnamon Filling Ingredients:

  • 3 tablespoons butter cold, roughly diced into inch or inch and a half pieces
  • 1/4 cup brown sugar
  • 2 tablespoons maple syrup
  • 1/4 teaspoon cinnamon
  • 1/8 teaspoon salt
  • 1 teaspoon pure vanilla extract

Frosting Ingredients:

  • 1/4 cup softened butter
  • 1/2 cup powdered sugar
  • 1 teaspoon pure vanilla extract

Instructions
 

Shortbread Cookie Instructions:

  • Prep and Preheat: Preheat your oven to 350°F (175°C). Line your baking sheet with parchment paper.
  • Cream together: In a mixing bowl, add 1/2 cup softened butter, and 1/4 cup + 2 tablespoons superfine white sugar caster sugar, cream together until light and fluffy. Add 1 1/2 teaspoons pure vanilla extract and mix until fully incorporated.
  • Mix Dry Ingredients: In a separate bowl, whisk together 1 1/4 cups + 1 tablespoon all-purpose flour and 1/8 teaspoon salt.
  • Combine Wet & Dry Ingredients: Gradually add the dry ingredients to the butter mixture, mixing until just combined to avoid overworking the dough.
  • Chill: Cover the dough and place in the fridge to chill for 15-30 minutes before baking. This is a great time to start working on the filling (instructions below).

Cinnamon Roll Filling Instructions:

  • Cook: In a heavy bottom sauce pan, add 3 tablespoons butter, 1/4 cup brown sugar, and 2 tablespoons maple syrup. Warm medium low heat until the sugar and butter have melted. The moment the butter has melted, take it off the heat and transfer to a heat-proof bowl.
    Add 1/4 teaspoon cinnamon, 1/8 teaspoon salt and 1 teaspoon pure vanilla extract to the heated butter/sugar mixture and stir until fully combined.
  • Chill: The mixture will be runny while hot, but once it cools it will thicken. You can put the filling in the fridge or freezer for just a few short minutes to speed up the process, but don't let the filling freeze. We're targeting room temperature.

Assemble and Bake:

  • Roll into balls: Once the dough is ready, use a 1.5-inch cookie scoop to create the cookie dough balls. We use TWO scoops per cookie and merge them together, rolling into a ball. Place each cookie ball on the prepared cookie sheet.
  • Form the cookies: Using the back of the cookie scoop, make a well in the middle of the dough ball by pressing down in the top center of the cookie to make an indent where we will add the pecan filling. If the cookie cracks you can either leave it as is (I don't mind cracks!), or you can gently press the cracks with your finger to bring together the two parted sides.
  • Bake: Place the pan of unfilled cookie dough balls in the oven and bake at 350 for about 15-minutes or until the cookie is no longer shiny.
  • Add the Filling: When the cookies are out of the oven, and still hot, carefully reinforce the dip in the middle using the back of the cookie scoop used earlier. Because the cookie is still hot (please be careful!) it will adjust to the shape.
    Once the cinnamon roll filling and cookies have cooled to room temperature, spoon the filling into the well in the middle of the baked cookies, being careful to only place in the center. Allow the filling to set further while you make the frosting.
  • Cream together: In a mixing bowl, combine 1/4 cup softened butter, 1/2 cup powdered sugar, and 1 teaspoon pure vanilla extract. Mix until smooth and creamy.
  • Frost: Transfer the frosting to a piping or zip lock bag and pipe it in a swirl on top of the cinnamon filling.
  • Serve and Enjoy!: The cookies may be eaten right away or they can be served later on. The filling will continue to set with time, but it's not necessary to wait for it to set. The cookies may be stored in the fridge in an air-tight container. However, you’ll want to bring them to room temperature before serving.

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