Ultimate Oreo Stuffed Cinnamon Rolls (Black Cocoa Twist)

In my American kitchen, Sunday mornings have a soundtrack, the clink of a glass of milk, the hush before the oven door opens, and that first breath of cinnamon-sugar warmth. Oreos were always “Milk’s Favorite Cookie,” but cinnamon rolls were the weekend comfort food that made everyone wander in, hair messy, smiling.

These oreo stuffed cinnamon rolls are the mashup I wish I’d made years ago, fluffy enriched dough, dark cookie flavor, and a gooey center that tastes like a bakery special. I’ll walk you through dough feel, proofing, and the black cocoa trick that makes the Oreo vibe unmistakable.

Why You’ll Love This Recipe

Black Cocoa Magic: Black cocoa powder gives that signature Oreo depth, darker, more intense, and less like “regular chocolate cake.”

Brown Butter Upgrade: In my kitchen, browning the butter for the filling turns sweet into sophisticated, nutty, toasted notes that make the brown sugar filling taste grown-up.

Enriched Dough Comfort: Whole milk, butter, and egg create an enriched dough that bakes up plush, not bready, and it stays tender even after the glaze sets.

Bakery-Style Swirls: The dental floss method keeps those spirals crisp and dramatic, so every roll looks like it came from a pastry case.

Ingredients and Substitutions

These rolls use everyday baking staples, with black cocoa and crushed Oreos doing the heavy lifting for that cookies-and-cream flavor.

Ingredients

Chocolate Oreo Cinnamon Roll Filling:

• 1/2 cup packed light brown sugar 100g
• 2 Tbsp black cocoa powder 12g
• 1 tsp ground cinnamon 3g
• 1/4 cup unsalted butter, softened – to be spread on the dough 56g
• 1/2 cup crushed Oreos 50g

Oreo Cinnamon Roll Dough:

• 3 1/2 cups all-purpose flour + up to 1/2 cup addition flour to be added later in process 440g-500g
• 2 tsp or 1 packet instant dry yeast 7g, 1/4 oz.
• 1 tsp fine salt 6g
• 1 cup whole milk 240g
• 1/2 cup granulated sugar 100g
• 1/4 cup unsalted butter, room temperature 56g
• 1 large egg, room temperature 56g
• 1/2 cup crushed Oreos 50g

Vanilla Glaze:

• 1 Tbsp unsalted butter, room temperature 8g
• 1 1/2 cups powdered sugar 188g
• 2 Tbsp whole milk 30g
• 1 tsp artificial vanilla extract 4g

Ingredient Notes & Substitutions

Black cocoa powder: This is the “Oreo note,” deep color, low acidity, and a distinct cocoa bitterness that reads like cookie, not brownie. If you swap in standard Dutch-process, it’ll still be good, but the flavor will drift toward classic chocolate cinnamon rolls.

All-purpose flour: All-purpose flour gives a tender bite, which is exactly what I want for a soft roll. Bread flour works if you like chewier, taller swirls, because the higher protein builds more structure.

Whole milk: Whole milk makes a richer enriched dough and helps the crumb stay soft on day two. Lower-fat milk can work, but the rolls won’t feel quite as plush.

Instant yeast: Instant yeast is forgiving and fast, which is why I use it for weekend baking. Keep your milk mixture warm, not hot, so the yeast stays lively.

Oreos: For the best texture, I like a mix of fine “dust” and small chunks, dust tints the dough, chunks give you little cookie surprises. Double Stuf is delicious too, it just melts a bit more into the filling.

How to Make oreo stuffed cinnamon rolls

Build the flavor base and warm the oven

1. In a medium sized bowl, mix together 1/2 cup packed light brown sugar 100g, 2 Tbsp black cocoa powder 12g, and 1 tsp ground cinnamon 3g, then set it aside.
2. Preheat your oven to 200 F / 95 C, this is just to create a cozy proofing spot later.
3. For the “black cocoa brown butter” twist, brown 1/4 cup of the butter in a small saucepan until it smells nutty and toasted, then let it cool back down until it’s spreadable. Keep the process the same later when you spread the butter, you’re just adding that toasted depth.

Mix the dough until tacky, not sticky

1. In a large bowl or the bowl of a stand mixer, combine 3 1/2 cups all-purpose flour + up to 1/2 cup addition flour to be added later in process 440g-500g, 2 tsp or 1 packet instant dry yeast 7g, 1/4 oz., and 1 tsp fine salt 6g.
2. In a separate microwave safe bowl, add 1 cup whole milk 240g, 1/4 cup unsalted butter, room temperature 56g, and 1/2 cup granulated sugar 100g.
3. Heat on high power for 60-90 seconds, until the mixture is warm to the touch and the butter is melted, then stir until smooth.
4. Gradually add the warm milk mixture into the flour mixture and mix on medium speed with a dough hook until the dough comes together.
5. Add 1 large egg, room temperature 56g, then mix on low until a sticky dough ball forms. Keep mixing on medium-low for 2-3 minutes, until the dough looks more elastic.
6. Add additional flour 1 Tbsp at a time until the dough begins to leave the sides of the bowl. The best test is a poke, it should feel tacky but not sticky, and your finger should lift away clean.
7. Mix in 1/2 cup crushed Oreos 50g on medium speed until they’re incorporated throughout the dough, you’ll see a speckled, cookies-and-cream marbling.

Rest, roll, fill, cut, proof, bake, and glaze

1. Cover the bowl with plastic wrap and let the dough rest for 10 minutes. You’re looking for that little “fogging up” inside the wrap from the dough’s warmth.
2. Generously flour your counter and roll the dough into a 12 inches x 18 inches rectangle, about 1/2 cm thick.
3. Spread 1/4 cup unsalted butter, softened – to be spread on the dough 56g over the dough, leaving 1/2 inch on the long side uncovered. If you browned the butter earlier, this is where that toasted aroma earns its keep.
4. Sprinkle the filling evenly over the buttered area, then top with 1/2 cup crushed Oreos 50g.
5. Tightly roll the dough horizontally toward the uncovered strip, keeping tension so the swirl stays defined.
6. Cut the log into 9 equal pieces with dental floss, slide floss under, cross, and pull straight through, then place in a greased square pan (8 in x 8 in works perfectly).
7. Turn the oven off, yes, completely off.
8. Cover the pan with foil and place it in the oven for 30 minutes, or until the rolls have risen.
9. Remove the pan, take off the foil, then turn the oven back on and heat to 350 F / 175 C.
10. Bake for 26-30 minutes, or until the rolls are golden brown, rotating the pan halfway through so they color evenly.
11. For the glaze, mix 1 Tbsp unsalted butter, room temperature 8g, 1 1/2 cups powdered sugar 188g, 2 Tbsp whole milk 30g, and 1 tsp artificial vanilla extract 4g until smooth.
12. Let the rolls cool for 10-20 minutes, then drizzle on the glaze. If you glaze too early, it disappears into the heat instead of sitting pretty on top.

The Secrets to a Perfect Bakery-Style Rise

Oreo rolls can rise beautifully, but the dough needs the right signals: warmth, gluten strength, and just enough flour to hold air without turning dense.

Texture control, Oreo dust vs. chunks: I like finer Oreo “dust” mixed into the dough for color and flavor, and bigger bits saved for the filling so you still get crunch against the gooey brown sugar center.

Temperature precision: Cold milk or a cold egg can shock instant yeast and slow proofing. Aim for that cozy 110°F feel, warm like bathwater, never steaming.

Gluten and kneading: Good kneading builds stretch, so the dough can trap the yeast’s gases and lift. The phrase develop the gluten to allow yeast bread dough to stretch and rise explains the goal perfectly.

Humidity awareness: That extra 1/2 cup of flour is truly as-needed, because a muggy kitchen makes dough stickier. The same instincts you’d use with artisan bread apply here, add flour slowly until the dough is tacky, not messy.

If your dough doesn’t rise in 30 minutes: Leave it in the warm, turned-off oven a bit longer, and confirm your yeast is fresh. If the oven was left on by accident, start over, overheated dough won’t recover well.

Pro Tips & Troubleshooting

Pro Tips

• Use the dental floss method for every cut, it keeps that clean spiral and prevents squishing.
• Rotate the pan halfway through baking, especially if your oven has hot spots.
• Let the glaze hit rolls that are warm, not piping hot, so it stays opaque and luscious.
• A final sprinkle of black cocoa or a mini Oreo on top makes them look bakery-finished.

Common Mistakes to Avoid

• Adding all the flour at once, the dough can turn dry and tough fast.
• Forgetting to turn the oven off during proofing, heat can kill the yeast.
• Icing while the rolls are too hot, the glaze melts into a thin, glossy puddle.
• Using cold milk or a cold egg, which can slow proofing and dull the rise.

Serving & Storage

Serving Ideas

Serve these warm with a tall glass of cold milk, it leans right into that milk-and-cookies nostalgia. For a bigger dessert table, the same crowd that loves these usually goes wild for an Oreo cake recipe, especially at birthdays and game-day spreads.

If you want to go over-the-top, set out a little dip on the side, cream cheese whipped with Oreo crumbs is my guilty pleasure for extra swirls.

Storage & Reheating

Store leftovers in an airtight container once fully cooled, they’ll stay soft for day two and beyond. For the best “fresh-baked” feel, microwave a roll for 15-20 seconds with a small cup of water nearby, the steam revives the enriched dough.

For overnight rolls, assemble and cut, cover the pan well, and proof in the fridge. In the morning, let the pan sit out while the oven heats, then bake at 350 F / 175 C as written, adding a few minutes only if the dough is still chilly.

FAQ

Conclusion

When you pull these from the oven, the smell is pure comfort, cinnamon, toasted butter, and that deep black cocoa Oreo perfume. The brown butter twist is the little chef’s secret that makes them taste like you paid too much at a fancy bakery.

If you bake them, I hope you’ll show off those swirls, they’re half the fun. And if you’re in a cinnamon-roll mood again, a batch of cinnamon roll muffins is another cozy way to keep the weekend sweet.