bittersweet baking chocolate or semi-sweet chocolate, roughly chopped
In This Recipe
For the dough:
Whisk together flour, baking powder, and salt in a medium bowl. Set aside.
In a large bowl, mix water, vegetable oil, sugar, and eggs until combined. Slowly stir in the flour mixture, mixing until the dough begins to come together. Turn the dough out onto a flat surface and knead a few times with your hands until it is smooth, but not sticky. (If the dough appears too dry, knead in more water, 1 teaspoon -- and no more! -- at a time. If it looks too wet, knead in up to 1/4 cup more flour, 1 tablespoon at a time, until you reach the right consistency.)
Gather the dough, then divide it in half with a knife and form into two flat disks. Wrap each disk tightly in plastic wrap and refrigerate for at least 3 hours, or up to overnight.
For the filling:
Use a spice or coffee grinder to grind the poppy seeds, working in batches if necessary, until powdery, 15 to 20 seconds.
In a small saucepan set over medium heat, combine the milk, sugar, ground poppy seeds, and apricots. Bring to a simmer, then turn the heat to low and cook, stirring frequently, until almost all the liquid is absorbed and the mixture thickens, 7 to 10 minutes.
Add the orange juice, lemon juice, and butter and cook until absorbed, 2 to 3 minutes. Stir in the chocolate and vanilla and cook, stirring continuously until the chocolate melts and the mixture is very thick, 2 to 3 minutes more. Remove from the heat and let cool slightly before filling hamantaschen. If desired, make up to 2 days ahead and store, covered, in the refrigerator.
Preheat the oven to 350° F and line a large rimmed baking sheet with parchment paper. Remove half of the dough from the refrigerator (keep the other half wrapped and chilled). On a lightly floured work surface, roll the dough to 1/8-inch thickness. Use a 3-inch round cookie cutter or glass to cut out as many circles as possible and carefully transfer them to the prepared baking sheet, leaving about 1/2 inch between each. Gather the dough scraps, re-roll, cut out additional circles, and transfer them to the baking sheet.
Spoon 1 teaspoon of filling into the center of each dough circle. Fold the left side over on an angle, followed by the right side. Fold the bottom flap up, tucking one end under the side flap to make a triangle-shaped pocket (the filling should still be visible in the center); pinch the seams firmly to seal. Repeat the process with the remaining dough and filling.
Bake until lightly golden and browned at the corners, about 15 to 18 minutes, until the cookies are cooked through. Remove from the oven and let the cookies cool on the baking sheets for 5 minutes, then transfer to a wire rack to cool slightly. These are best served warm. Store in an airtight container in the refrigerator for up to 3 days. Reheat leftovers briefly in a toaster oven.