Chocolate-Orange Sandwich Cookies


This copycat cookie recipe looks like the much-loved Milano cookies you buy at the store, but the cookie texture is more tender than crisp.

Chocolate-Orange Sandwich Cookies
Photo: Carson Downing
Hands On Time:
45 mins
Total Time:
1 hr 30 mins
22 sandwich cookies


  • 1 ½ cup butter, softened

  • 1 ⅓ cup powdered sugar

  • ¾ cup granulated sugar

  • ¼ teaspoon salt

  • 4 eggs

  • 2 teaspoon orange zest

  • 1 teaspoon vanilla

  • 2 ⅔ cup all-purpose flour

  • 2 cup dark chocolate chips

  • 1 cup heavy cream


  1. Preheat oven to 400°F. Line two cookie sheets with parchment paper.

  2. In a large bowl beat butter, powdered sugar, granulated sugar, and 1/4 tsp. salt with a mixer on medium until very light and fluffy. Beat in eggs, one at a time, until combined. Beat in orange zest and vanilla. Beat in flour.

  3. Transfer dough to a large pastry bag fitted with a 1/2-inch round tip or a gallon-size resealable bag with the corner snipped off. For each batch, slide cookie template* under the parchment on prepared cookie sheet. Pipe dough onto parchment to fill template outlines. Remove template.

  4. Bake 8 to 10 minutes or until edges are just beginning to turn golden. Let cool on a wire rack.

  5. For ganache: Place chocolate chips in a medium bowl. Heat cream in a small saucepan over medium until it begins to simmer (do not boil). Pour hot cream over chocolate; let stand 5 minutes. Gently stir until smooth. Let cool 20 to 30 minutes or until ganache is room temperature and of spreading consistency, stirring frequently.

  6. Spread bottoms of half of the cookies with ganache. Top with remaining cookies. Let stand until ganache is set. Makes 22 sandwich cookies.


A template makes it easier to pipe equal ovals. Create the template by drawing 2 1/2×1 1/4-inch ovals 2 inches apart onto a sheet of parchment paper.

Nutrition Facts (per serving)

374 Calories
24g Fat
39g Carbs
4g Protein
Nutrition Facts
Servings Per Recipe 22
Calories 374
% Daily Value *
Total Fat 24g 31%
Saturated Fat 15g 75%
Cholesterol 79mg 26%
Sodium 150mg 7%
Total Carbohydrate 39g 14%
Total Sugars 26g
Protein 4g
Vitamin C 0.3mg 2%
Calcium 19mg 1%
Iron 0.9mg 5%
Potassium 44mg 1%
Fatty acids, total trans 1g
Folate, total 33mcg
Vitamin B-12 0.1mcg

*The % Daily Value (DV) tells you how much a nutrient in a food serving contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.

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