These soft and buttery cookies are as fun to make as they are to eat. This raspberry Hamantaschen is a family recipe that involves a chilled butter dough that gets rolled and shaped into little triangles. This version calls for raspberry preserves, but you could try apricot too.
Cream together the butter and sugar until light and fluffy in a stand mixer fitted with a paddle.
While mixing, add the vanilla, salt, orange juice, and egg, mixing well until creamy.
Sift flour into the bowl and mix on low to form a crumbly dough.
Gather any dry flour and mix a bit to form a smooth dough. Try not to over-knead the dough, just stop when it comes together. Wrap tightly in plastic wrap and flatten a bit (this will make life easier when you go to roll it out later). Refrigerate for 3 hours or overnight.
Preheat oven to 350°F and line 2 baking sheets with parchment paper.
On a lightly floured surface, roll the dough until 1/4" thick and stamp 3" circles. Add a level teaspoon of jam in the center and fold one side, then overlap with another flap, and another to form a triangle where the corners meet and press together.
Place formed cookies on a plate and refrigerate while you work. Refrigerating helps the cookies keep their shape. Bake for 20 minutes or until the dough is lightly golden. Cool on a wire rack and store in a plastic bag or container with a tight lid.
The purpose of the chilled dough is 2-fold. First, it's easier to roll the dough when chilled. Second, the little triangular shapes will hold their shape better if the dough is chilled. You can keep 1/2 of the dough in the fridge while you work or you can refrigerate the cookies before baking.
Shaping the Triangles
Forming hamantaschen triangles is a bit of an art. If the jam gets in-between the dough edges, the seal will likely not form and these cookies will spread open during baking. Make sure to use a small amount of jam (level teaspoon for 3-inch circles) and press the edges together firmly to seal. Practice and chill the dough as you work for best results.
How to Soften Butter
You can soften butter on the counter for 1 hour or put in the microwave on the defrost setting for 20 seconds. Butter is soft when you can press your finger into it easily like play dough (but not liquid).