Brownie Filled Triple Chocolate Hamantaschen Recipe

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Chocolate lovers rejoice with this brownie filled triple chocolate hamantaschen recipe! When you’re done, check out my big list of hamantaschen recipes too. This post contains affiliate links.

If you ask me, in life, the more chocolate the better.

A few years ago, after jotting in my notes never ever to do hamantaschen again unless I have a death wish, I had a brilliant idea.

If I turned my favorite hamantaschen dough by Tori Avey into a chocolate variety, fill it with brownie batter, and then dip them into deeeliscious dark chocolate, maybe, just maybe, I SHOULD do hamantaschen again.

I tried it a couple of years ago, and while I didn’t have time to replicate it and photograph last year (blame soon-to-be Baby Jay), I made it happen this year and I’m excited to show you the results.

I’ve officially modified my recipe to say “don’t to hamantaschen again UNLESS there’s lots of chocolate involved, AND no kids are present, AND cup of coffee is close by.”

In all seriousness, dipping and coating these brownie filled chocolate hamantaschen opened up the creative side of baking (which I find sorely lacking creativity in general, and so I generally prefer cooking). I had fun drizzling peanut butter, dipping in crushed almonds, and both. I even quadrupled the chocolate factor by crushing some chocolate chips and dipping in that too…

So I present to you this brownie filled chocolate hamantaschen recipe with a dough adapted from Tori Avey’s recipe.

They are not only delicious, but they make a gorgeous Purim party centerpiece, as they present beautifully. Just spread them on your favorite wooden board.

The chocolate hamantaschen dough is a bit on the thicker/drier side of things, and needs to be used right away, but it has a fabulous texture. It’s more cookie than cake, and has a fabulous crunch.

And complete with the brownie filling, and the crunch of nuts and hardened chocolate, it’s fabulous.

Of course, just like any hamantaschen recipe, adapt it as you’d like. Use the chocolate hamantaschen dough with other fillings, or use the brownie filling hack with non-chocolatey dough…

And the best part? The recipe makes extra brownie batter! I got a bonus pan of (thin) brownies in for the same effort!

I didn’t pull out my Kitchen Aid for this, though I did use a hand mixer for the brownie batter.

Triple Chocolate Hamantaschen Recipe

Ingredients

Brownie Hamantaschen Filling

I used a box of Duncan Hines brownie mix to fill them, because why fix what isn’t broke? You can likely use any brownie batter for this, but if it’s too runny, it might not work as neatly.

• Box Duncan Hines brownie mix
• 1/3 C water
• 1 Egg
• 1/3 C oil (I used extra light olive oil, vegetable or canola oil work too)

Chocolate Hamantaschen Dough

• 2  Eggs
• 2/3 C Sugar
• 1/4 C oil (I used extra light olive oil, vegetable or canola oil work too)
• 1 t vanilla sugar
• 1 3/4 C flour
• 1 C Cocoa
• 1 t baking powder
• 1/4 t salt
• 2 T water
• Extra flour for dusting

For dipping

• 1 cup chocolate chips (I like Trader Joe’s gold package)
• Toasted almonds, chocolate chips crushed, peanut butter… or whatever you like!

Note: you can cut your circles with a round glass or with a cookie cutter. A cutter definitely makes cleaner cuts, but in a pinch, a glass works too! I showcased this recipe with a glass.

Process

1. Mix together brownie ingredients. Chill in the fridge for 1 hour or a little more. It should be less flowy, and pretty much hold its shape when you spoon some onto a surface.

2. Preheat your oven to 350.

3. Mix together the eggs, sugar and oil.

4. Add the dry ingredients – vanilla sugar, flour, cocoa powder, baking powder, water (you can mix them together first if you want to do things properly – I skip that because I’m lazy.)

5. Mix them together. I used a spoon until all the wet was incorporated, and then went in with my hands. When it’s looking dry and crumbly, add the water.

6. When your dough looks workable – not breaking apart, but not sticky either, roll it out on a clean, floured surface.

Roll it to a good, consistent thickness using a floured rolling pin. I went as thin as I could without it breaking, but it can depend on your preference.

7. Cut out circles of dough using a 3 inch round cookie cutter, or a glass in a similar size. I used plastic wrap for some – it helps form a neater cut – but ditched it halfway through. Did I mention I’m lazy? Take the scraps, smush them together (add a bit of water if it’s too dry) and roll them out again. Keep going until your dough is used up or too hard to work with.

8. Arrange your circles on 2 baking sheets. Place a teaspoon of brownie batter on each. It should roughly hold its shape. You many want to test one hamantasch for batter quanity before doing the rest. Do NOT overfill.

9. Assemble your hamantaschen pinwheel style, if you like it when they stay shut. Fold over one side, then the other overlapping the first at the corner, and then the last side, overlapping the previous side at the corner, and tucking the other corner under the first fold.

10. Pinch together to keep it shut.

Note: on later hamantaschen, you may find that some of the flour is sitting at the surface. Since these are chocolate hamantaschen, it’ll show more than on non-chocolate. You can wipe those off, or gently went those sides after you’ve assembled these.

You may have extra brownie batter at this point! Simply bake yourself some brownies. I spread it in a 9×13 because I like my brownies thinner, and topped it with slivered almonds.

11. Bake for 25 minutes, or until a toothpick inserted into the brownie center comes out clean.

12. Chill in the fridge overnight.

13. Place your chocolate chips into a microwave safe measuring cup and microwave for 1 minute. Stir. Microwave in 30 second increments, stirring in between until it’s smooth and melted. Meanwhile, prepare your toppings. I crushed some toasted almond slivers by placing them in a ziploc bag and hammering them with a meat tenderizer.

14. Dip a corner of your hamantaschen into the chocolate and then into the topping. If using peanut butter, place in a glass and microwave for 30 seconds, drizzle over your chocolate hamantaschen.

Tip: if you have a corner that’s not as nice, dip that one!

Allow to cool completely (I recommend placing your baking sheets in the fridge for a few hours). Store in an airtight container, or freeze. This chocolate hamantaschen recipe is incredible when served frozen too!

Enjoy your brownie filled triple chocolate hamantaschen recipe!

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