Recipe Details

Prep Time:
45 mins
Cook Time:
45 mins
Chill Time:
4 hrs 50 mins
Total Time:
6 hrs 20 mins
42 cookies


  • 1cupunsalted butter, softened

  • ¾cupwhite sugar

  • 2largeeggs

  • 1tablespoonvanilla extract

  • 3 ½cupsall-purpose flour, plus more for dusting

  • 1tablespoonbaking powder

  • ¼teaspoonkosher salt

  • cupwhole milk

  • 3tablespoonsunsalted butter

  • 2ouncesbittersweet chocolate, finely chopped

  • 6tablespoonswhite sugar

  • ½teaspoonvanilla extract

  • ¼teaspoonkosher salt

  • 1largeegg

  • 1tablespoonall-purpose flour

Cooking Directions

  1. Prepare dough: Beat butter and sugar at medium speed with a stand mixer fitted with the paddle attachment until combined and creamy, about 1 minute.

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  2. Add eggs, 1 at a time, and beat until just combined after each addition, stopping to scrape down the sides of the bowl as needed; beat in vanilla just until combined, about 30 seconds.

  3. Whisk together flour, baking powder, and salt in a medium bowl.

  4. Add flour mixture to butter mixture alternately with milk, beating at low speed, until combined, about 1 minute.

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  5. Divide dough in half and shape each into a disk. Wrap each in plastic wrap and chill for at least 4 hours, or overnight.

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  6. Prepare filling: Place butter and chopped chocolate in a small microwave-safe bowl. Melt in microwave on high (100%) power for 1 to 1 1/2 minutes, stirring every 20 seconds, until melted and smooth.

  7. Stir in sugar, vanilla, and salt until fully combined (mixture will look grainy). Stir in egg and flour until completely combined and smooth. Chill for 30 minutes.

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  8. Preheat the oven to 350 degrees F (175 degrees C). Line baking sheets with parchment paper.

  9. Remove 1 dough disk from the refrigerator and divide in half; cover and keep 1 dough half in refrigerator. Roll dough out on a floured surface until 1/8 inch thick; using a 3-inch round cutter, cut dough into circles (only re-roll scraps once).

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  10. Place dough rounds on prepared baking sheets, about 1 1/2 inches apart.

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  11. Top each dough round in the center with 1 level teaspoon of the chocolate filling (keep filling in refrigerator when not in use). Fold one edge inwards, slightly covering the filling. Fold the next edge slightly overlapping, and then the last, creating a triangle with overlapping sides so you still can see an almond-sized amount of the filling. Press dough down to ensure dough sticks together.

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  12. Chill in a freezer for 10 minutes or in a refrigerator for 30 minutes. Repeat procedure with remaining dough and filling.

  13. Bake in the preheated oven in the middle rack, in batches, until lightly browned around bottom edges and bottoms, 12 to 14 minutes.

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  14. Cool completely on wire racks about 10 minutes.

Cook’s Notes:

The dough gets soft really quickly – keep unused dough refrigerated. Don’t re-roll scraps but one time as it makes the cookies very tough. It’s important to keep your hands clean and free of filling to keep a clean-looking cookie as an end result.

These can be kept chilled until ready to bake, or frozen and placed in heavy-duty zip-top bags and baked when ready.

Nutrition Facts

Full Nutrition Label
Servings Per Recipe42
% Daily Value *
Total Fat
Saturated Fat
Total Carbohydrate
Dietary Fiber

* Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs.

** Nutrient information is not available for all ingredients. Amount is based on available nutrient data.

(-) Information is not currently available for this nutrient. If you are following a medically restrictive diet, please consult your doctor or registered dietitian before preparing this recipe for personal consumption.

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