Instructions

Make the dough:

1. *This step needs to be made ahead of time and chilled at minimum 3 hours to overnight in the fridge.
2. Slice room temperature butter into small chunks and place in a large mixing bowl.
3. Add sugar to the bowl. Use an electric mixer to cream the butter and sugar together for a few minutes until light and fluffy.
4. Add the egg, vanilla, and orange zest to the bowl. Beat again till creamy and well mixed.
5. Sift flour and salt into the bowl. Mix with the electric mixer on lowest speed until a crumbly dough forms.
6. Begin to knead dough with hands until a smooth dough ball forms. Try not to overwork the dough, only knead until the dough is a smooth consistency.
7. If the crumbles are too dry to form a smooth dough, add water slowly, 1 teaspoon at a time, using your hands to knead the liquid into the dough. Knead and add liquid until the dough is smooth and slightly tacky to the touch (not sticky), with a consistency that is right for rolling out. It can easily go from the right consistency to too wet/sticky, so add water very slowly. If the dough seems too wet, knead in a little flour until it reaches the right texture.
8. Form the dough into a flat disk and wrap tightly in plastic wrap. Place in the refrigerator to chill for 3 hours to overnight.

Make the compote:

1. Start by washing, peeling, and cutting your apples of choice into ½” pieces, and wash the raspberries, picking out any leaves/twigs.
2. In a medium saucepan, combine apples, raspberries, brown sugar, and butter over medium-low heat.
3. Stir frequently until butter is melted and sugar is dissolved, then add cinnamon, vanilla extract, salt, and cornstarch. To better incorporate the cornstarch, mix desired amount into the cold water and dissolve with a spoon fully before adding to the apple mixture.
4. Increase heat to medium and bring to a rolling simmer. Simmer for 5 minutes, stirring occasionally so raspberries don’t burn.
5. Use a potato masher or big fork to mush apples and raspberries into a smaller, more jam-like consistency. The apples may not smush as well, but that’s alright for this recipe.
6. You may need to cook this a little longer or add more cornstarch if the compote isn't thickening to that jammy consistency. If using the cornstarch method, increase by 1 tsp. increments, combining with a little cold water to dissolve before adding. A little cornstarch goes a long way!
7. Remove from heat and allow mixture to cool at least 15-20 mins. before including in the cookies.

Make the Hamantaschen:

1. Start by heating the oven to 350*F.
2. Lightly flour a smooth, clean surface. Unwrap the dough disk and place on the floured surface. The dough will be very firm after chilling.
3. Use a rolling pin to roll the dough out to 1/4" thick. At the beginning, it will be tough to roll out-- you may need to pound it a bit. A heavy rolling pin works best.
4. As you roll, cracks may form on the edges of the dough. Repair any large cracks by pressing back together with your fingers and continue rolling. Lightly flour the rolling pin occasionally to prevent sticking.
5. Use a circular 3" wide cookie cutter (not smaller) or the 3-inch rim of a glass to cut circles out of the dough, cutting as many as you can without re-rolling it.
6. Gather the scraps and roll them out again. Cut circles. Repeat process again if needed until you've cut as many circles as you can without having to re-roll the dough too much (about 3-4 times re-rolled and the dough begins to dry out). You should end up with around 25-35 circles.
7. Place a teaspoon of filling (whichever filling you choose) into the center of each circle. Do not use more than a teaspoon of filling, or you run the risk of your hamantaschen opening and filling spilling out during baking. Cover unused circles in waiting with a lightly damp paper towel to prevent them from drying out while you are filling.

Assemble the Hamantaschen:

1. First, grasp the left side of the circle and fold it towards the center to make a flap that covers the left third of the circle.
2. Grasp the right side of the circle and fold it towards the center, overlapping the upper part of the left side flap to create a triangular tip at the top of the circle. A small triangle of filling should still be visible in the center.
3. Grasp the bottom part of the circle and fold it upward to create a third flap and complete the triangle. When you fold this flap up, be sure to tuck the left side of this new flap underneath the left side of the triangle, while letting the right side of this new flap overlap the right side of the triangle. This way, each side of your triangle has a corner that folds over and a corner that folds under-- it creates a "pinwheel" effect. This method if folding is not only pretty-- it will help to keep the cookies from opening while they bake.
4. Pinch each corner of the triangle gently but firmly to secure the shape. If any cracks have formed at the places where the dough is creased, use the warmth of your fingers to smooth them out. Repeat this process for the remaining circles.
5. When all your hamantaschen have been filled, place them on a parchment lined, lightly greased baking sheet, evenly spaced.
6. Place in the oven and bake at 350*F for 10-25 minutes, until the cookies are cooked through and lightly golden brown. Start checking them at 10 minutes; because the dough thickness tends to vary on these cookies, they can cook quite fast if rolled thin. In most ovens, it will take around 15-20 minutes, but best to keep a close watch over them as they cook to avoid overcooking or burning.
7. Cool the cookies on a wire rack. Store them in a tightly sealed plastic bag or Tupperware for up to two weeks in the fridge.

Notes:

1. We also used pre-made jams or marmalade as fillings for the cookies along with the compote above if you'd like quicker options. The compote was the most popular flavor, however, more traditional fillings include poppy seed, apple, prune, and apricot. Check out the link below to see more filling options from the author of the dough recipe!