Notes: Original recipe from Barbara Steppel from Jewish Creative Cooking cookbook, with technique and modifications documented by Debra Steppel
Dough (makes 5 dozen)
Ingredients
1 and 1/3 cups vegetable shortening (best taste is with Butter Flavored Crisco sticks which are pareve)
1 cup granulated sugar
2 eggs
2 tsps real vanilla extract
1/2 cup orange juice (for pareve) or milk (if dairy)
4 cups flour (original recipe said to sift the flour but I never sift it and results work just fine with a lot less work)
Directions
Using an electric mixer, cream together the shortening and sugar.
Add eggs, one at a time, and continue beating until blended.
Add liquid and vanilla; continue beating until fully combined.
Mix in the flour (1 cup at a time -- for the last cup of flour I mix by hand so as not to break the mixer when the dough starts to become too thick for the electric mixer).
Combine well until a ball of dough is formed and all ingredients are thoroughly mixed.
Divide the dough into 5 approximately equal sections. Shape each section into log shapes (each log will become 1 dozen hamantaschen) and wrap (airtight) each log in plastic wrap. Put the 5 wrapped logs into a Ziploc bag to really keep the air out.
Refrigerate at least several hours or preferably overnight.
When you are ready to form and bake the hamantaschen, give yourself plenty of time (several hours) as it always takes longer than expected. (Faster with helpers!)
Preheat oven to 400 degrees before starting to roll out the first batch of dough. Keep the dough cold until ready to roll it out.
Place about 18" length of plastic wrap on the counter. Place one log of dough on the plastic wrap, then another 18" layer of plastic wrap on top of the dough (between the dough and the rolling pin). Roll a log of dough to about 1/8" thick.
Use a drinking glass as a cookie cutter to make circles about 3" in diameter. I usually roll out the dough, cut 4-6 circles, smoosh the excess dough from the outsides of the circles back up into a ball, roll it out again to 1/8" thick to make 4-5 more circles, smoosh the leftovers into a ball again, and finally roll whatever's left to make the last few circles. Repeat with each dough log.
Use a flat spatula to remove the dough circles from the plastic wrap and place on large cookie sheets lined with parchment paper (parchment paper prevents the bottoms from getting too dark and prevents them from sticking to the pan). Hamantaschen dough doesn't spread when baking, so you can place the dough circles fairly close together (not quite touching).
Place about 1 tsp of filling* in the center of each dough circle and form them into a triangle just as shown on this video:
https://toriavey.com/how-to/how-to-make-perfect-hamantaschen/
Bake at 400 degrees for about 10 minutes, until edges just begin to turn golden brown. Remove pan from oven and allow to cool 2-3 minutes before removing to a cooling rack.
*Filling Notes
Traditional hamantaschen are poppyseed (mohn). The best one is Solo brand in a can, usually on the bottom shelf near the pie fillings (baking aisle) in most supermarkets. A 12.5 oz. can of Solo pie filling is enough to fill about 2 - 2.5 dozen Hamantaschen. Most pie filling flavors can also be used. Common flavors are apricot, strawberry, apple, raspberry, or blueberry. Pie filling works better than jam because jam tends to spread and make a mess on the baking pan.
Less-traditional fillings are prune/raisin/walnut (recipe below), Hershey Kiss, Nutella, guava cheesecake (cream cheese and guava paste), PB&J (1/2 tsp each of grape or strawberry jam and peanut butter), or s'mores (crumbled graham cracker, a mini marshmallow, and a few chocolate morsels).
A much faster way to place filling on the dough circles is to spoon the filling into a pastry bag or Ziploc bag and cut off a tiny corner (about 1/2") then squeeze the filling from the bag corner onto the dough circles, one at a time.
Prune/raisin/walnut filling recipe:
In a food processor, blend 18 pitted prunes with 1/4 cup boiling water to form a paste (or use 3 jars of prune baby food). In a small saucepan, boil together the prune puree, 1/3 cup raisins (remove stems), 1 tsp lemon juice, and 1/3 cup of chopped walnuts for about 5-10 minutes, until it heats through and thickens. Stir about every minute to prevent burning on the bottom of the saucepan.
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