Photo credit Yael Buechler
Prep Cook Yield Ready In
40 minutes + 3 hours (or more) resting time 8-10 minutes 4 dozen cookies 50 active minutes plus 3 hours resting time

Caramel Macchiato Hamantaschen Recipe

This Purim treat pairs perfectly with your favorite cup of coffee.

Hamantaschen are one of my favorite Jewish foods to bake — and eat. As a child, I remember helping my mother to gently tape wax paper to our wooden kitchen table to prepare for the sticky mess that would ensue when rolling copious amounts of hamantaschen dough. I think this was the only time we used wax paper — and I still stock it in my own kitchen for this occasion.

This recipe for Caramel Macchiato Hamantaschen was adapted from the “The Spice and Spirit of Kosher-Jewish Cooking” by Esther Blau, which was a staple cookbook in my home growing up. While I am a hamantaschen purist, loving the simplest of apricot-filled hamantaschen, I decided to expand my hamantaschen repertoire with this creation. These easy hamantaschen are soft and sweet on the outside, with the perfect inside burst of melted espresso morsels in a juicy caramel sauce.

I use Nestle Toll House Espresso Morsels and the caramel-flavored Smucker’s Sundae Syrup, but any espresso baking chips or caramel syrup would work. 

Note: The hamantaschen dough needs to refrigerate for a few hours, and preferably overnight.

When you are ready to roll the dough, have the following items nearby to make the rolling process smoother:  

  • Rolling surface (wax paper, a silicone baking mat or flat plastic cutting board)
  • 1 cup of flour in a bowl 
  • Rolling pin (if you don’t have a rolling pin, try an unopened wine bottle or tall plastic cup) 
  • Plastic cup (about 3.5 inches in diameter) 
  • Prep bowl filled with caramel syrup
  • Prep bowl filled with espresso baking chips 
  • Spoons for caramel and chips
  • Prep bowl with ½ cup water 
  • 4 baking trays with greased baking sheets on them


For the dough:

  • ½ cup margarine, vegan butter or unsalted butter, melted 
  • ½ cup canola oil
  • 1 cup sugar
  • 3 eggs
  • ½ cup orange juice (store-bought is fine)
  • 2 tsp baking powder
  • 4 cups flour

For the filling: 

  • ½ cup espresso baking chips
  • cup caramel syrup + extra to drizzle on top once baked


  1. Melt ½ cup of margarine. Combine the melted margarine with ½ cup of canola oil and 1 cup sugar in a large bowl. 
  2. Add 3 eggs (I check each one individually for blood spots in a small bowl first) and stir them into the mixture. 
  3. Pour in ½ cup of orange juice and mix. 
  4. Slowly add 2 cups of flour and the baking powder. Add the remaining two cups of flour and mix until all of the dough is clumped together. 
  5. Cover the bowl of dough and place into the refrigerator to rest for a few hours or overnight.
  6. Preheat your oven to 350°F. 
  7. Place dough on your lightly floured rolling surface, one handful at a time (this makes the rolling process more manageable). Sprinkle flour on your rolling pin and roll the handful of the dough until it’s about 1/8 of an inch thick. Continue to gently add flour on your dough if it is too sticky. 
  1. Use a plastic cup to twist out circles in the dough and place these circles on your baking sheets (spaced about 1 inch away from each other). 
  2. Add 3-4 espresso baking chips and ½ teaspoon of caramel syrup to the center of each circle. 
  3. Fold the circles into a triangle in the shape of Haman’s hat and pinch the corners tight. Dip your fingers into the bowl of water and gently dampen the corners of the hamantaschen to help the hamantaschen remain sealed while they bake in the oven. Caramel is a softer filling so having a tight seal on your corners is helpful. 
  4. Bake the hamantaschen for 8-10 minutes at 350°F until golden. Let them cool on a separate cooling tray or plate. 
  5. If you are serving your Caramel Macchiato Hamantaschen right away, drizzle caramel sauce on top. If you are saving your hamantaschen for later (which is tough because they are so delicious), place them in containers and save the drizzling for when it is time to serve them.

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