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Cookie Butter-Stuffed Chocolate Challah

Cookie Butter Chocolate Challah

The combination of deep, dark chocolate and silky, sweet cookie butter is rich and delicious, without being over the top. You can also try stuffing this chocolate challah dough with other favorite fillings, including peanut butter, raspberry jam, or even white chocolate for a beautiful contrasted challah.

You can also use this challah recipe and follow the directions below to make Chocolate Cookie Butter Rugelach.

Cookie butter chocolate rugelach step 1

Remove a chunk of chocolate challah dough (the size of your palm) and roll dough on a floured surface, 1/16-inch thick, in a circular shape.

Cookie butter chocolate rugelach step 2

Spread 2 tablespoons canola oil over dough and sprinkle with 3 tablespoons sugar. Spread cookie butter (about ½ cup) over dough.

Cookie butter chocolate rugelach step 3

Cut dough to make about 16 triangles. Roll triangles to form rugelach, by rolling larger side towards smaller side. Bake in a 350°F oven for 20 to 25 minutes.

Cookie butter chocolate rugelach step 4

Combine ¼ cup hot water and ¼ cup sugar and brush over warm rugelach. Eat immediately.

  • Duration
  • Cook Time
  • Prep Time
  • 1 large challah or 2 smaller challahsServings



  • 1 ½ tablespoons dry yeast
  • 1 ¼ cups lukewarm water
  • 1 teaspoon sugar
  • ½ cup dark cocoa powder
  • 4 cups unbleached all-purpose flour, plus extra for dusting
  • ½ tablespoon salt
  • ½ cup + 2 tablespoons sugar
  • ¼ cup vegetable oil
  • 1 teaspoon pure vanilla extract
  • ½ teaspoon cinnamon
  • Pinch nutmeg
  • 2 eggs
  • 1 cup cookie butter (link above), peanut or almond butter, for filling


  • 1 egg, beaten with 1 teaspoon water
  • Crushed tea biscuit cookies (optional)
  • ½ cup sugar (optional)
  • ½ tablespoon cinnamon (optional)
  • Coarse sea salt (optional)


1. In a small bowl, place yeast, 1 teaspoon sugar, and lukewarm water. Allow to sit around 10 minutes, until it becomes foamy on top.

2. In a large bowl or stand mixer fitted with the whisk attachment, mix together ½ cup cocoa powder with 1 cup flour, salt, sugar, vegetable oil, vanilla, cinnamon, and nutmeg. After the water-yeast mixture has become foamy, add to flour mixture. Mix thoroughly.

3. Add 1 cup of flour and eggs and mix until smooth. Switch to the dough hook attachment if you are using a stand mixer.

4. Add 1 cup of flour, mixing thoroughly, and then remove from bowl and place on a floured surface. Dough will not feel firm yet, but that’s what you want. Knead remaining 1 cup flour into dough, continuing to knead for around 3 minutes. You can add slightly more than 1 cup flour if needed, but the dough should still feel light, otherwise your challah will turn out too dense.

5. Place dough in a greased bowl and cover with a damp towel. Allow to rise at least 3 hours or up to 4 hours.

6. Preheat oven to 350°F. Depending on whether you are doing a three-, four-, or six-strand braid, divide dough into sections. Roll each section into a rope and then flatten slightly. Generously spread a few tablespoons cookie butter down the center of each flattened strand. Fold the challah over the cookie butter and pinch tightly. Roll out the rope one more time. 

7. Braid challah into desired shape. Allow challah to rise another 45 to 60 minutes, or until you can see the size has grown and challah seems light. This step is very important to ensure a light and fluffy challah.

8. In a small bowl beat 1 egg with 1 teaspoon water.

9. Brush egg wash liberally over challah. Sprinkle with crushed tea biscuit cookies if desired. If you cannot find tea biscuit cookies, combine ½ cup sugar with ½ tablespoon cinnamon and sprinkle on top along with thick sea salt.

10. If making one large challah, bake around 27-28 minutes; if making two smaller challahs, bake 24-26 minutes. Serve warm.

Recipe published in JOY of KOSHER with Jamie Geller magazine Winter 2015. Subscribe Now.

JoyofKosher with Jamie Geller Chanukah Magazine