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Homemade Gluten-Free Milano Cookies Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.1 from 79 reviews
  • Author: Bara
  • Prep Time: 15 minutes
  • Cook Time: 11 minutes baking + 15 minutes crisping
  • Total Time: 36 minutes
  • Yield: 13 servings
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Gluten Free

Description

These homemade Milano cookies are a delicate and delicious treat featuring a crisp buttery cookie with a smooth chocolate filling. This recipe offers a gluten-free option using Bob's Red Mill gluten free all-purpose flour and yields perfectly shaped cookies that are ideal for sandwiching with melted semisweet chocolate. The cookies are baked until golden and then left to crisp up in the warm oven before being paired with rich chocolate for a classic homemade Milano experience.


Ingredients

Cookie Dough

  • 1/2 cup butter (at room temperature)
  • 1 cup powdered sugar
  • 1 large egg (at room temperature)
  • 1 tsp vanilla extract
  • 1¼ cup gluten free all purpose flour (I used Bob's Red Mill)
  • 1/2 tsp sea salt

Chocolate Filling

  • 3/4 cup semisweet chocolate chips


Instructions

  1. Preheat and Prepare Baking Sheets: Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper to ensure the cookies bake evenly and do not stick.
  2. Cream Butter and Sugar: In a large bowl, use an electric mixer to cream together the room temperature butter and powdered sugar until the mixture is light and fluffy, creating a smooth base for the dough.
  3. Add Egg and Vanilla: Add the egg and vanilla extract to the creamed mixture and beat thoroughly until all ingredients are well incorporated, ensuring a uniform dough.
  4. Incorporate Dry Ingredients: Add the gluten-free all-purpose flour and sea salt to the wet ingredients and mix just until combined, careful not to overwork the dough which can toughen the cookies.
  5. Pipe the Dough: Transfer the dough into a piping bag or resealable plastic bag with a 1-inch corner snipped off. Pipe 3-inch long logs onto the prepared baking sheets, spacing each about 1 inch apart. The shape does not have to be perfect as the dough will spread and even out while baking.
  6. Bake and Crisp Cookies: Bake the cookies for 10-11 minutes until the centers are set. Then, turn off the oven, leave the door slightly ajar, and let the cookies crisp up inside the warm oven for 15 minutes. This step ensures a crunchy texture.
  7. Cool Cookies: Remove the baking sheets from the oven and use a spatula to transfer the cookies to a cooling rack. Let them cool completely before assembling the sandwiches.
  8. Melt Chocolate: Melt semisweet chocolate chips in a double boiler or microwave in 30-second increments, stirring in between until smooth and fully melted without burning.
  9. Assemble Cookie Sandwiches: Spread a spoonful of melted chocolate onto the flat side of one cookie, then sandwich it with another cookie. Press gently to spread the chocolate evenly. Repeat this process with all cookies and allow the chocolate to set before serving.

Notes

  • Ensure butter and egg are at room temperature for best mixing and texture.
  • Don’t overmix the dough once flour is added to keep cookies tender.
  • Leaving cookies in the warm oven after baking helps achieve the classic crisp texture of Milano cookies.
  • Use parchment paper on baking sheets for easy cleanup and to prevent sticking.
  • Chocolate can be tempered for extra shine and snap but melted chocolate works great for a quick filling.
  • Store cookies in an airtight container to maintain freshness.