Chocolate-filled Hamantaschen: or was that a Mexican wedding cookie?

When are hamantaschen also Mexican wedding cookies?

When the recipe is inspired by both! And then what shall we call them? Mexican wedding hamantaschens? Or chocolate-filled hamantaschen with Mexican flavors or a Fiesta Hamantaschen. No matter what we call them, they are a brand new cookie created for a beautiful couple - Emma and Héber - with Mexican and Jewish heritage who wanted to reflect that in their wedding festivities.

Skip the story and Jump to Recipe

I worked with the bride-to-be, Emma, to help her and her fiancé figure out what they wanted the cookie to communicate about their backgrounds, their wedding and their future as a couple. She realized that hamantaschen were a happy Jewish food memory for her and that her husband's Mexican heritage should be baked into the recipe too.

Mexican wedding cookies (also known as polvorones) made sense as inspiration for the dough. Also, Emma and Héber love Mexican chocolate with a hint of cinnamon so I chose a babka style chocolate filling from my cookbook and modified it to include Mexican chocolate flavors.

When the couple came over for the first tasting, I was nervous! What if they weren't happy (though my previous tasters all assured me these were a big win). I prepared the cookie 3 ways - like a traditional Mexican wedding cooking with no filling so they could really taste the dough; like a thumbprint cookie; and as a traditional hamantash. A quick sprinkle of powdered sugar finished all three versions.

They were thrilled with the chocolate-filled hamentaschen exactly as made! Phew!!! Meanwhile, my husband, aka as our in-house barista, made them espressos to drink with the cookies which is how they intended to serve them. The happy couple recommend café de olla - coffee, cinnamon and piloncillo (sugar) as the perfect accompaniment.

And when they made the cookies on their own for their aufruf, the text I received was: "They were so easy, and very fun, to make!!!! Thank you!!!!" And after the event: "People at the aufruf loved them!"

Now let's learn to make these beautiful chocolate-filled hamantaschen!

Equipment needed to make the hamentaschen

Ideally, I recommend the following tools/kitchen equipment:

• A food processor for the nuts and dough
• A rolling pin
• Round cookie cutters
• Parchment paper
• Baking sheets

Ingredient and substitutions

Don't be intimidated by the specialized Abuelita Mexican-style hot cocoa mix - I actually found it in a big box store right next to the other instant cocoa mixes. I'll offer alternatives below. (don't I always??!! 😘)

For cookie dough:

• Pecans: I suggest using unsalted raw pecans, giving them a quick toast in the oven (I use a toaster oven and set a timer so I don't burn them!)
• Butter: Use unsalted butter so you have control over how much salt is in the dough recipe.
• Powdered Sugar: Powdered sugar is a classic ingredient in Mexican wedding cookie doughs for texture.
• Kosher Salt: Just a reminder that I always use Diamond Crystal kosher salt for my recipes. If you are using Morton's kosher salt, for example, it is saltier so please use about half the amount.

For chocolate filling:

• Mexican-style hot chocolate: The inspiration for the flavor of the filling came from the bride and groom who love to drink Abuelita hot cocoa which has a hint of cinnamon. Turns out this hot cocoa mix is easy to find in your local big box store right where the other hot chocolate mixes are. But if you can't find it, use one packet of regular hot cocoa mix and add an extra ½ teaspoon of cinnamon.
• Instant coffee: Use the fine-ground espresso powder also available in your local big box store or online from baking specialty supplier King Arthur.
• Dark chocolate: I usually keep high quality chocolate chips in the house for baking - I pick them up at the market any time I see them for a decent price. But any kind of dark chocolate will work - it can be a bar or chips. Chips are just so quick and easy to use!

Let's make these Jewish cookies step-by-step!

(Printable recipe card is at the end of the post with ingredients, measurements and step-by-step instructions. This section includes more and larger pictures and high level explanations of the process.)

Skip this section and Jump to Recipe

Make the dough:

1. Using the food processor, chop the pecans until almost finely ground. Then add the powdered sugar. Pulse to combine then remove the nut mixture and set aside. 

2. Add the flour, granulated sugar and salt to the processor bowl pulse a couple times just to combine. Add cubed cold butter and process until the flour mixture is coarse with no giant lumps of butter. 

3. Add nut mixture back in and pulse to combine then add egg and pulse until the dough comes together.

Roll out and rest the dough:

4. Once the egg is well incorporated, turn the dough onto a piece of parchment paper or clean surface. Divide the dough in half, flatten each half into a disk and roll out between two pieces of parchment to between ⅛ and ¼ inch thick. (Alternatively, you can wrap each disk and refrigerate and roll out later). Place rolled out dough on a cookie sheet and into the fridge to chill for 20 - 30 minutes.

Make the filling:

5. While the dough is chilling, make the filling by placing the chocolate chips and butter in a microwave safe bowl. Melt chocolate and butter in the microwave at 50% power for a minute at a time. Remove after each minute and mix with small wooden spoon or spatula.

6. Once the chocolate butter mixture is completely smooth and shiny, add the rest of the filling ingredients and mix well. Let this chocolate mixture cool down before filling the hamantaschen. Yields 1 cup of filling.

Form and bake the cookies:

7. Remove one dough piece from the refrigerator, grab your 2.5” - 3” round cookie cutter and make cutouts in the dough – as many as you can fit – then remove the scraps and place the parchment with the round dough pieces on a cookie sheet. If the dough is really cold and stiff, let it warm up enough so you can form each round into a triangle.

8. Place a heaping teaspoon of the cooled filling in the center of each dough round. Use your thumbs and forefingers to cinch the dough into a triangle, creating 3 corners. Combine the scraps and re-roll. Refrigerate the re-rolled dough again and while it re-chills, work on the other half of the dough from the refrigerator.

9. Preheat oven to 375°F. Chill the formed cookies for 20 - 30 minutes then bake at 375°F for 15 minutes. Each oven is different so start checking about 2 minutes early – at 13 minutes. The underside of the cookies and the top edges should start browning. If cooking two sheets at the same time, switch shelves halfway through baking. Once removed from the oven, let the cookies cool in place for a couple minutes then move to a cooling rack.

10. To serve, place the chocolate-filled hamantaschen on a serving tray of choice and dust with powdered sugar just like you would with a Mexican wedding cookie!

Beth's expert tips and tricks

1. It may seem like a lot of steps, but this is just the nature of hamentaschen. Remember the dough can be made ahead, the filling can be made ahead and once you get into a rhythm, you’ll realize that while one batch is chilling, another batch can be forming and another batch can be baking. 
2. Many hands will make light work of baking these. And even if you are baking alone, you can fill the “chill time” with other parts of the baking process or just other kitchen or work chores.
3. Anytime the dough seems hard to work with, it’s probably just too warm. Pop it back in the fridge for 10 minutes or even the freezer for 5 minutes.
4. If you have a hard time removing the cut out rounds or the scraps even when the dough is properly chilled, a dough scraper is your friend! Just tuck it under the edge of the dough. It’s a magical tool. 
5. If you cinch up a hamantash and notice a crack or dent in the dough or notice that one dough round is way thicker than another, just smooth over the crack or press down the lump. This dough is malleable. 
6. If you make the filling ahead and it gets cold and hard, just reheat in the microwave at 50% power for at most a minute and check to see if it’s getting warm and soft again.
7. If you make the dough ahead (like hours or days) and roll it out as instructed, be sure to store the rolled out dough airtight so it doesn’t dry out. Either cover the sheet pan or store in one of those giant ziploc bags. You can also store it as a disk and roll out later, but it’s nice to have it rolled out and ready to go.

Other Purim recipes on OMG! Yummy

P.S. If you try this recipe, please leave a star rating and/or a review in the comment section below. I so appreciate your feedback! AND find more inspiration on Pinterest, Facebook or Instagram. Signup for my email list, too!