Great-Grandma Jennie's Hamantaschen

Step 1

Cream the butter and sugar in a large bowl of a stand mixer on medium high speed until it is light and fluffy.

Step 2

Add the eggs one at a time, beating well and scraping after each incorporation.

Step 3

Whisk the flour, baking powder, and salt together in a separate, large bowl.

Step 4

Add half the flour mixture to the butter and sugar mixture, and mix on low speed to combine.

Step 5

Add in the orange juice and vanilla on low speed.

Step 6

Add in the remaining flour mixture and mix on low speed to combine.

Step 7

Divide the dough in two and wrap in plastic wrap.

Step 8

Freeze for 30 minutes or refrigerate for several hours.

Step 9

Preheat the oven to 375° F.

Step 10

Roll out a quarter of the dough between two sheets of wax paper to between 1/8" and 1/4" (this method works by far the best).

Step 11

Use an upside-down cup to cut circles out of the dough.

Step 12

If any point the dough becomes too soft to easily work with, return to the freezer for 5 minutes.

Step 13

Lift the circles carefully onto a silpat or baking paper–lined cookie sheet.

Step 14

Depending on the size of your circles, spoon between 1/2 tsp and 1 tsp of filling in the center of each circle.

Step 15

Fold three sides of the circle in to make a triangle shape, and pinch the edges.

Step 16

Freeze the shaped hamentaschen 10 minutes before baking (this helps them keep their shape).

Step 17

Re-roll scraps and repeat to make more.

Step 18

Any left over dough can be frozen for several months.

Step 19

Bake one tray at a time for 15 minutes at 375° F.

Step 20

After 15 minutes, remove the tray from the oven and brush each cookie with the egg wash.

Step 21

Return to the oven for 5 minutes, or until the cookies are lightly golden-brown.

Step 22

Let cool on a wire rack.