Yeasted Poppy Seed Hamantaschen

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1. 1Step 1: Prepare the filling: Using a food processor, pulse cookies until you have fine crumbs. You can alternately do this using a rolling pin and a ziplock bag. Scrape the cookie crumbs out of the food processor if using, and set aside.
2. 2Step 2: In a spice grinder, pulse the poppy seeds a few times until they are finely ground.
3. 3Step 3: In a small saucepan over medium heat, bring milk, sugar, honey and lemon zest to a light boil.
4. 4Step 4: Add poppy seeds and stir constantly for 2 to 3 minutes, until thickened.
5. 5Step 5: Add the butter and 1/2 cup of the cookie crumbs, and the rest if needed, to achieve a thicker texture and sweeter flavor. Let cool completely before using.
6. 6Step 6: Fill a piping bag or zipper top bag with the cooled filling and snip off the end. Set aside until it's time to assemble the hamantaschen.
7. 7Step 7: Make the dough: In a medium bowl combine flour, sugar, salt and yeast, stirring after each addition.
8. 8Step 8: Using your fingers, work butter into the flour mixture until it resembles coarse crumbs.
9. 9Step 9: Add the eggs, most of the milk, vanilla and orange zest and mix until a cohesive dough forms. Add more milk or water if necessary, to bring together a dough that is soft but not sticky.
10. 10Step 10: Knead on a lightly floured work surface until smooth and elastic. Form into a ball and place dough back in the bowl. Cover and let rise several hours until tripled in size.
11. 11Step 11: Assemble the hamantaschen: Roll risen dough into a 1/8-inch-thick circle. Using a 4-inch biscuit or cookie cutter, cut out as many circles as possible. Repeat the process by bringing together the dough scraps and rerolling.
12. 12Step 12: Pipe one tablespoon of filling into the center of each circle. Go over the circles again with a rolling pin if they have puffed up.
13. 13Step 13: Dip your pinky finger into the egg wash and trace it around the edge of the circle. Fold up three edges and meet in the middle to make a triangle shape. Using more egg wash, make sure to firmly seal all edges.
14. 14Step 14: Place on a parchment paper-lined tray and repeat the process, leaving a few inches in between each hamantasch. Brush with egg wash and let rise 40 minutes to 1 hour, until puffy in appearance.
15. 15Step 15: While hamantaschen are rising, preheat your oven to 350°.
16. 16Step 16: Brush cookies again with egg wash and bake for 15 to 20 minutes, until golden.
17. 17Step 17: Make simple syrup: While hamantaschen are baking, combine all ingredients in a small saucepan and bring to a rapid boil. Turn off heat when the sugar has dissolved and the liquid has thickened slightly.
18. 18Step 18: Brush 1 to 2 tablespoons of hot syrup over each hamantasch immediately after they come out of the oven.
19. 19Step 19: Eat hamantaschen immediately, or wrap tightly and eat within one day. Reheat in the microwave for a few seconds to refresh. Otherwise, freeze to keep fresh and defrost as needed.