Chocolate Hamantaschen

Step 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.

Step 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.

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

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

Step 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.

Step 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.

Step 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.

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

Step 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).

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

Step 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.

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

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

Step 14
Cool completely on wire racks about 10 minutes.