Neapolitan Zebra Hamentashen

February 9, 2015

I don’t even know what to say about these hamentashen. They are just so much fun. Every year I try to come up with new creative hamentashen ideas that will push the envelope just a little bit further. While I think that no hamentahen recipe I think up will ever be quite as popular as the s’more hamentashen I made a few years back, I think these might just come close.

There is nothing quite as classic as the neopolitan flavor combination of strawberry, vanilla, and chocolate. I wanted to highlight those flavors in these hamentashen not only with the filling but in the dough as well. And frankly, I wanted them to look cool too. Part of what makes neopolitan ice cream so fun is the stripes of the different flavors. I knew I wanted the layers to stay distinct in the finished cookies (which is why I called them zebra cookies, because of the stripes.)

I considered layering the doughs and then cutting out slices and circles like Melinda did in her awesome rainbow hamentashen. But to be perfectly honest, that just seemed like a lot of work. Then I realized there was an easier way. I simply layered the doughs and rolled it up into a log like I would to make slice and bake pinwheel cookies. After chilling the dough it was easy to cut circles of the swirled dough, perfect for filling and folding into hamentashen.

No more rolling required. To enhance the flavors I filled the hamentashen with a strawberry and chocolate filling. The end result is quite striking. If you make these they are sure to be the talk of the town.

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Ingredients & Quantities

For Basic Dough (you will need to make this three times, once with each set of additions)
  • 1 1/2 cups(6.75oz, 190 g) flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/2 cup (3.75 oz) sugar
  • 1/4 cup (2 oz) margarine, cut into 8 pieces
  • 1/4 cup (2 oz )shortening, cut into 8 pieces
  • 1 beaten egg
  • 1 teaspoon vanilla extract
  • 1-2 tablespoons ice water
For Strawberry Dough
  • 1.5 ounce freeze dried strawberries, ground to a fine powder in the food processor plus an extra egg yolk
For Vanilla Dough
  • one large vanilla bean
For Chocolate Dough
  • 3 Tablespoons cocoa powder
For Filling
  • 1 cup good quality strawberry preserves
  • 3 tablespoons cornstarch
  • 1/4 cup finely chopped semi sweet chocolate

Cooking Instructions

Make the Strawberry Dough:

Place the strawberry powder and the rest of the dry ingredients in the bowl of a food processor (flour through sugar) and pulse to combine. Add the margarine and shortening and pulse until mixture resembles a coarse meal. Add the beaten egg and pulse until combined.

Remove the mixture from the food processor and pour into a large bowl. Press the dough together gently. If it makes a ball it is done. If it is still crumbly sprinkle the dough with one tablespoon of ice water and mix until it comes together into a smooth ball. If the dough still seems too dry add the remaining water until the dough just comes together.

Flatten the dough into a disk, wrap in plastic wrap and refrigerate for one hour.

Make the Vanilla Dough:

Follow the instructions above but add the scraped out seeds of the vanilla bean to the flour mixture in place of the strawberries.

Make the Chocolate Dough:

Follow the instructions above but add the cocoa powder to the dry ingredients in place of the strawberries.

Make the Hamentashen:

Place the strawberry dough between two pieces of parchment paper and roll it into a rectangle that is approximately 10 inches by 12 inches. It should be about a half inch thick. Set the strawberry dough aside.

Repeat with the other two doughs.

Peel the top piece of parchment off each of the doughs. Invert the vanilla dough on top of the strawberry dough and remove the bottom piece of parchment. Invert the chocolate dough on top of the vanilla dough. Using a sharp knife trip the rectangle to an even 10 x 12. Starting on one of the long sides carefully run a spatula between the edge of strawberry dough and the parchment. Carefully roll up the dough. It is helpful to run the spatula under the strawberry dough every few inches to keep it from sticking as it rolls. The dough may crack a bit as it rolls, that is fine. Just gently pinch it back together. Once the dough it all the way rolled up use the parchment paper to tightly wrap the dough log. Gently roll the log against the counter to make sure it is tightly rolled. Chill until firm enough to slice, at least two hours but preferably overnight.

Preheat the oven to 350. Combine the strawberry preserves and corn starch in a medium bowl and stir until well combined. Remove the dough roll from the refrigerator. Unwrap it and slice it into 1/4 inch slices. Rotate the dough log every few minutes to keep it from developing a flat side. The ends may not be as large or well swirled as the middle. Save the imperfect end scraps and press them together into circles for more abstract hamentashen.

Place each circle on a parchment lined baking sheet. Let the dough stand for 5-10 minutes to warm up. Fill with a scant teaspoon of the jam mixture. Sprinkle with a few small pieces of chocolate. Be careful not to overfill the hamentashen or they will burst open in the oven. Also, if there are any holes in the dough the filling will leak out in the oven so patch any cracks in the side of the hamentashen before baking. Fold two sides of the circle together, pinching tight to make a corner. Fold up the remaining side to make a triangle with the filling showing in the middle and pinch the other two corners well. It is important that they are well pinched, so that they do not come open in the oven.

Bake the hamentashen until they are slightly firm to the touch, 9-11 minutes. Remove from the oven and let cool for one minute. Transfer to cooling rack and let cool completely.

Recipe Times


1 Hour


10 Minutes


1 Hour 10 Minutes

Recipe Yield

Approximately 5 dozen

Recipe Categories


  1. LOVED the concept but the dough was too bland and crumbly.
    Ill try it again with butter and less baking powder. Raspberry dough was firm and tart, worth keeping.

    • I’m not exactly sure what you mean by crumbly. I had no problems with the dough crumbling at all. Did you measure the flour by weight? I agree that it isn’t the most flavorful dough, that is why I filled it with the combination of strawberry jam and chocolate to enhance the flavor. My go to dough recipe has an orange flavor with I thought would clash in this recipe. What is your favorite recipe?

  2. The dough breaks more easily than I like in the baked product, and crumbs fall away when take a bite, is what I mean by crumbly.
    I did measure the flour by weight, but it was nighttime, I might have mis-measured. And I used butter for half the shortening.
    After freezing and thawing, the flavor of the cookies improves!

    • I think the difference may be in the swap of fats. The shortening is critical to the texture of the cookies, it gives it a bit more chewiness which keeps it from crumbling. Sorry they didn’t work for you!

  3. These look great! Couple of questions before I try out the recipe: Can I substitute vanilla extract if I don’t have vanilla beans? And is it OK to chill the dough for more than an hour, or do I have to do everything the same day? Thanks!

    • Vanilla extract will work but the vanilla flavor will be less pronounced. It is totally fine to chill the dough overnight, an hour is just the minimum. Hope that helps.

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