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Chocolate Chip Cookie Cinnamon Rolls – The Ultimate Dessert Mashup

If you love cinnamon rolls and chocolate chip cookies, get ready for the ultimate treat—Chocolate Chip Cookie Stuffed Cinnamon Rolls!

If you’re new here, I love cinnamon rolls. For years I worked on perfecting and finding the BEST cinnamon roll recipe that isn’t too time consuming but also doesn’t take away from the sweet fluffy rolls I love.

I had seen a few creators experimenting with this combination over the past few months and I thought I had to try these. And you know what, they are super delicious. Both of these desserts compliment each other so well and I think you’re going to love them too!

This recipe brings together the soft, gooey swirls of a cinnamon roll with the rich, buttery goodness of a chocolate chip cookie, creating a dessert that’s out-of-this-world delicious.

Why You’ll Love This Recipe

Double the indulgence – Soft cinnamon dough with a melty chocolate chip cookie center.
Perfectly gooey – The warm, cinnamon-swirled dough pairs perfectly with the soft, baked cookie filling.
Homemade goodness – From-scratch dough and cookie dough make for an unforgettable sweet treat.

Ingredients:

For Starter

  • 30g water

  • 30g flour

  • 1/2 tsp instant yeast

For Dough

  • 178g (1/2 + 1/3 cup) warm milk

  • 17g (1 tbsp) greek yogurt or sour cream

  • 36g (2 1/2 tbsp) sugar

  • 8g (2 tsp) instant yeast

  • 56g (1) egg

  • 32g (2 tbsp) cold water

  • 380g (2 1/3 cup) flour

  • 19g (2 1/2 tbsp) cocoa powder

  • 15g (1 tbsp) food colouring

  • 5g (1 tsp) baking powder

  • 66g (1/4 cup) butter, room temperature

For Chocolate Chip Cookie Filling

  • 116g (1/2 cup) butter, room temp

  • 90g (1/3 cup) brown sugar

  • 58g (1/4 cup) sugar

  • 1 egg

  • 1 tsp vanilla

  • 208g (1 1/3 cups) flour

  • 8g (1 tbsp) cornstarch

  • 5g (1 tsp) baking powder

  • 1/2 tsp baking soda

  • 192g (1 1/3 cups) chocolate chips

For Cinnamon Sugar Filling

  • 28g (2 tbsp) butter, melted

  • 173g (3/4 cup) brown sugar

  • 3g (2 tsp) cinnamon

  • .75g (1/4 tsp) nutmeg

For Regular Icing

  • 220g (1.5 cup) icing sugar

  • 19.5g (1.5 tbsp) butter (melted)

  • 1.5 tsp vanilla

  • 48g (3 tbsp) heavy cream

OR

For Cream Cheese Icing

  • 170g cream cheese, softened

  • 78g butter, melted

  • 2 tsp vanilla extract

  • 340g (2 1/4 cups) powdered sugar

Directions:

  • Prepare the Starter

    • In a small bowl, combine 30g water, 30g flour, and ½ teaspoon instant yeast. Stir until fully incorporated.

    • Cover with plastic wrap and let it rest in a warm place for 1 to 1.5 hours, or until bubbly and active.

  • Prepare the Dough

    • Warm the milk to bath temperature in a medium bowl or cup. Stir in yogurt, sugar, and instant yeast, mixing well. Allow the mixture to sit for 10 minutes, or until frothy and activated.

    • In a separate large bowl, whisk together the flour and baking powder.

    • Once the yeast mixture is activated, beat in the egg, then pour it into the dry ingredients. Add the prepared starter and begin mixing with a kneading attachment.

    • Once the dough starts to come together, gradually incorporate butter in small chunks, then knead for 10 minutes until smooth and elastic.

    • Transfer the dough to a lightly oiled bowl, cover with plastic wrap, and let it rise in a warm place for 1 to 1.5 hours, or until doubled in size.

  • Prepare the Cookie Filling

    • In a large bowl, beat together butter and sugars until smooth and well combined.

    • In a separate bowl, whisk together the dry ingredients: flour, baking powder, baking soda, and cornstarch.

    • Add the egg and vanilla extract to the butter mixture, mixing until fully incorporated. Gradually add the dry ingredients, mixing until just combined.

    • Fold in the chocolate chips, cover the dough with plastic wrap, and set aside until ready to assemble.

  • Prepare the Cinnamon Sugar Filling

    • In a medium bowl, whisk together brown sugar, cinnamon, and nutmeg.

    • Cover and set aside until the dough is ready to roll.

  • Assemble the Cinnamon Rolls

    • Line a 9x11-inch baking pan with parchment paper and lightly grease it. Set aside.

    • Melt the butter in the microwave.

    • Once the dough has doubled in size, transfer it to a lightly floured surface and roll it out into a 12x18-inch rectangle, about ¼ to ½ inch thick.

    • Brush the melted butter evenly over the dough, then sprinkle the cinnamon sugar filling evenly on top.

    • Take the cookie dough and spread it over the cinnamon sugar layer, pressing gently to create an even layer.

    • Carefully roll the dough into a tight log, starting from the top. Slice into 1-inch rolls and arrange them in the prepared baking pan.

    • Cover with plastic wrap and let rise for 30 to 45 minutes in a warm place.

  • Bake the Cinnamon Rolls

    • Preheat the oven to 350°F (175°C).

    • Cover the cinnamon rolls with a buttered piece of foil and bake for 23 minutes. Remove the foil and bake uncovered for an additional 5 to 6 minutes, until golden brown.

    • Allow the rolls to cool slightly before icing.

  • Prepare the Icing

    • For either regular or cream cheese icing, whisk together all ingredients in a medium bowl until smooth and creamy.

  • Finish & Serve

    • Let the cinnamon rolls cool for 10 to 15 minutes, then generously drizzle with icing. Serve warm and enjoy!

Whether you’re making these for breakfast, dessert, or a special occasion, these stuffed cinnamon rolls are sure to wow everyone who takes a bite.

Thanks for reading Chez Alex Desserts! This post is public so feel free to share it.

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