Take about a quarter of the dough and roll it out to about 1/8 of an inch thick. Be sure to rewrap the rest of the dough and put it back into the fridge.
Use your 3″ round cookie cutter and cut out circles. Fill the hamentaschen with your filling of choice (we’ll get to that in a minute*) and fold the sides up to form a triangle. Reroll the scraps and cut out more circles, repeating until you’re done.
If you’ve never done this before or if you need a more visual reminder of some hamentaschen how-to, the Spice and Spirit cookbook has a great step-by-step tutorial. Or you can just Google it.
Once filled, place the hamentaschen directly on a foiled and greased or parchment-covered baking sheet.
Place the tray into the fridge for ten minutes to firm up the dough. Don’t skip this step. It sounds like a waste of time when you’re baking many trays of cookies, but firming up the dough before baking helps the hamentaschen retain their shape in the oven, which, from personal experience, is usually the cause of a hamentaschen’s downfall.
Brush the hamentaschen with a watered-down beaten egg and bake for 12-13 minutes (no really, not more than that – they may not look fully done, but they are) in a preheated 400° degree oven.
Let them cool, eat a few and freeze the rest – Purim is still pretty far away, but not that far and once it’s around the corner and you’re knee deep in mishloach manot ideas, costume searches and seuda preparations, you’ll be pretty thankful for the baking-marathon of a snow day. And the next time a snow day hits and your freezer is full of hamentaschen, you’ll be wishing for a second kitchen so you can get a head start on that Pesach baking. (I’m kidding. Totally kidding.)
*We’ve tried a pretty big assortment of hamentaschen fillings over the years, including all the different fruit preserves, peanut butter and chocolate, Nutella, M&M’s, Hershey Kisses and even chocolate chips in the dough itself – but last year we won the jackpot with brownie hamentaschen. Start with a box of Duncan Hines brownie mix – make the recipe for fudge brownies, not cake ones. Bake the brownies in a 9″x13″ for 15 minutes, way less time than it would take to fully bake the brownies. Let the brownies cool for a few minutes and then using a small spoon and the half-baked brownies, fill and fold the hamentaschen. Then bake the hamentaschen themselves in the oven. The brownies will fully bake in the center of the hamentaschen and won’t ooze out the sides because they are already half-baked. A win for everyone.