Hamentashen

That photo is of some Hamentashen my son and I delivered to friends tonight. As you can see, while they may not be quite as picture perfect in appearance as *some* recipe site photos I’ve viewed, I guarantee that if you follow the directions I give here, you’ll have people asking you for the recipe, too.
What I share here is based upon the very basic recipe I discovered more than 20 years ago in a Chabad Jewish Calendar. They still have this same recipe posted in their current calendar. If you have access to one, you can see this is very close to it, but I’ve made a few important clarifications and tweaks to make it even better. I’ve noted them primarily with parenthesis or asterisk or detailed explanation. This is NOT the same recipe I’ve seen on the Chabad website and that recipe isn’t nearly as good as their OLD CLASSIC recipe you’ll find on the calendar. I don’t like the recipe they have on the Chabad kids site, and it doesn’t even have the amount of flour correct. So be careful.
The first time I tried making hamentashen on my own I had an awful time. It was a MESS. My kitchen was a mess, I was a mess and the hamentashen was, too. The recipe I used wasn’t as good as this one and the dough never did taste as good. I’ve used several other recipes over the years. Some used apple juice, lemon juice, and vanilla extract, butter or other ingredients. I don’t use any of those anymore. The best tasting and most consistently praised dough is the one I share here.

Sometimes the mess of making hamentashen can be half the fun, and it’s been a family thing since my son began helping me when he was 2. Now he can make hamentashen as good as mine (He says better!)

With every other recipe, my dough was either too sticky or too dry or I couldn't get the sides to stick or my fillings were too runny or too much and oozed out or made the sides open, or despite using the required temperature setting and time indicated, I baked them too long and the bottoms were too dark. Or when I glazed them with just beaten egg alone as the Chabad recipe called for, the glaze was too hard and just too shiny.

So after more than 30 years of trial and error, here is the method I use to make Hamentashen
Ingredients:
1 cup sugar
1/3 cup vegetable oil
1/3 cup vegetable shortening
3 extra large eggs * original recipe didn’t note size of egg but it IS important
1/2 cup orange juice (through trial and error I believe it’s best if you can use fresh squeezed juice from Texas sweet oranges..and it really does make a difference)
4 cups unsifted *all purpose flour*
3 teaspoons baking powder
1 teaspoon salt
You’ll also need one more egg for later on in the recipe.
For the filling: The original recipe I started from said 2 pounds mohn filling ..I never measure how much I actually have to start with but it’s at least one can of prepared poppyseed filling and then other things as the whim strikes me or my family as to what we want to try inside!
Traditional filling is poppyseed (mohn) or prune or apricot fillings. Other common fillings include any fruit pastry or pie filling or combinations with chopped or crushed nuts. There are some recipes to make your own poppyseed filling or almond filling, but I choose not to go to that much trouble. I use the Solo brand that is available at Kroger and their almond filling alone and in combination with other ingredients.
This is the first year I've not made blueberry hamentashen. Since my son was 2, it was one of his favorites.
It requires a THICK blueberry pie or pastry filling or add
blueberries to anything thinner or it makes a mess and tries to open
the hamentashen while baking.

This year the chocolate chip/walnut/almond pastry filling has proven to be the favorite. I also enjoyed mixing strawberry preserves with the almond pastry filling.
The first batch I made with the chocolate chips was with white and
dark chocolate chips (and the white chocolate melts better) so you
can get away with just both of those. Then I ran out of the white chocolate and decided to just use dark chocolate chips and crushed walnut. I only made about a dozen of those and they were tasty but I felt needed more moisture since the chips didn’t melt enough so I added the Solo brand almond pastry filling and created a new family favorite. It was a perfect texture and the blend of flavors is yummy.
You can experiment with many different fillings before you find what you like best but you must at least try the traditional poppyseed hamentashen! They all taste excellent dunked in a cold glass of milk. Oh, I’m getting ahead of myself..back to the recipe.
Now here is how you put it all together:
In a large bowl mix sugar, oil and shortening to creamy texture together. Then scramble up 3 extra large eggs in a separate bowl, add to sugar/oil/shortening mix then add the 1/2 cup orange juice. Mix these ingredients until you have a very creamy smooth texture. Next, add the 4 cups flour, the baking powder and the salt. Mix all of those ingredients to form the dough. Now, another tweak to make a better dough to work with is to divide it into at least two sections, put in a covered container and refrigerate for a MINIMUM of an hour. You can make your dough one day and refrigerate the dough overnight to finish baking the next and that’s fine, too.
Next, spread out a sheet of wax paper on your work surface. Lightly flour the paper and take one of your portions of chilled dough and lightly flour to roll it out with
a rolling pin about ½ a centimeter thin. Using a drinking glass or mug as a dough cutter, cut a circle (about 3 inches across is the size glass I use). Then
place a dollop of the filling into the middle of each circle. If you
put too much in, they will either tend to open or the contents spill
out while baking. For us old fogeys to get an idea of the proportion of filling to put on the dough circle, think of an old 45 record..and the center label section and you'll get an idea of the proportion of filling to the dough. Think of the filling as the label. If you’re not old enough to get a mental image of a 45 record, the original recipe says 1/2 to 2/3 tsp but that's just a guideline. In those pictured above, I believe I used closer to a whole teaspoon of filling. Then pinch up the sides tightly to make a triangle.

The original calendar Chabad recipe tells to put them on greased cookie sheets. I don't do that. I use aluminum foil on my cookie sheet and take each batch off the sheet by lifting the whole foil and setting them to the side to cool and then
place more foil on for the next batch :) I've never had them stick to the foil.
I often make 2 or 3 'sets" of dough as I did yesterday with 2 batches of dough. While I'm rolling, cutting and filling the next dozen hamentashen on a sheet of aluminum foil, the first set is baking.

The very last step before you put them into a preheated 350 degree oven: take
that last egg and beat that with 1 tablespoon of water until it is fluffy then brush it over each hamentashen for a light glaze.

The recipe says bake approximately 20 minutes and it is important to pay attention to that word approximately.

I discovered a long time ago that for my oven and this recipe, it takes exactly 18 minutes...20 minutes is too long for my oven. Experienced bakers know that altitude and humidity and other factors also may make a difference and will learn to adjust recipes for that, too. I recall that across town with a different oven I always baked them 21 minutes. So it is important to pay close attention that "ovens may vary".

When the bottom is slightly golden, they're done. Don’t overcook them.

The Chabad calendar recipe said it yields 4 dozen hamentashen. I’ve never managed to make that many out of it. With the 3 inch diameter glass I use to cut the dough I get anywhere from 36 to 40 hamentashen, not 4 dozen. Yesterday I made 75 hamentashen from 2 batches of dough.

Making hamentashen with kids is a very fun thing to do. It can still be fun as they grow older and then it becomes a family tradition. Many small Children LOVE to roll the dough and cut it and get sticky icky with all the fillings. It is also a longstanding tradition for children to deliver baskets and trays of hamentashen to friends, neighbors and shut-ins. Son and I delivered the tray of 18 hamentashen pictured above to some friends across town this evening. When I can, I prefer to give 18 rather than a dozen because Jews often give gifts and donations in multiples of 18, which is called "giving chai". Since Purim is a celebration of the fact we survived an attempt to eliminate us, the 18 hamentashen is my way of focusing on Judaism honoring LIFE itself.
Shalom y’all.

Enjoy!

EDIT: I forgot to mention that sprinkling confectioner's sugar over the top is also a nice added touch. Obviously, I also forgot to buy some to sprinkle on the hamentashen I made yesterday!

SECOND EDIT:
I received the following today in my email:
Top Ten Reasons for Celebrating Purim
by Kenneth Goldrich

1. Making noise in shul is a MITZVAH!!
2. Levity is not reserved for the Levites
3. Nobody knows if you're having a bad hair day. You can tell them
it's your costume
4. Purim is easier to spell than Chanukah, I mean Hanukah, I mean,
KHanukah, I mean Chanuka, I mean the Festival of Lights.
5. You don't have to kasher your home and change all the pots and
dishes.
6. You don't have to build a hut and live and eat outside (but you
could volunteer to build a new Purim booth for next year's Carnival)
7. You get to drink wine and drink wine and drink wine and you don't
even have to stand for Kiddush (I guess you can't!)
8. You won't get hit in the eye by a lulav
9. You can't eat hamantaschen on Yom Kippur
10. Mordecai - 1 ; Haman - 0 !!!!