If regular homemade cinnamon rolls were married to semisweet chocolate, you'd get these gooey and over-the-top pastries with chocolate in the filling and topping. A double dose, just in case. The dough can be made ahead, and the baked rolls can be frozen; another reason to make these often.

Single chocolate glazed roll on a white plate. Light gray background.

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Rich and gooey

The smell in your kitchen makes it impossible to resist them.

It's a classic cinnamon roll dough filled with cocoa and chocolate chips and drizzled with a chocolate glaze. A lot, I know, but worth it.

I strongly feel pastries, in general, should be eaten within a few hours of baking them, just like muffins. They will never be as good if you ask me. That said, warming them up will revive a day old pastry and make them worth eating.

I'm all about the little things and these chocolate rolls can brighten up a dull day.

Testing Notes

These have an intense chocolate flavor. So, if you want a lighter dose, use less glaze or less cocoa powder in the filling. For sweeter rolls, use milk chocolate chips instead of semisweet.

Achieving a gooey texture: Don't skimp on the butter and sugar in the filling, and make sure you don't overbake the rolls. The center must be cooked (no wet dough) but still soft and doughy.

Flat or dense rolls: Check the yeast first to avoid throwing the whole thing into the trash. Second, allow the dough to rise sufficiently in a warm environment. If your kitchen is cool, it might take longer. The dough should roughly double in size.

Cinnamon chocolate rolls with chocolate glaze on a dark pan. Golden server.

Ingredient Notes

Quantities are listed in the recipe card towards the end of this post. The Ingredients page has more details and lists the brands we use.

Chocolate: Use your favorite semisweet chocolate for this recipe.
Cocoa powder: Always use unsweetened. In my experience, the dark ones are the best (this does not apply to the super dark used for making homemade Oreo cookies known as dark or black cocoa powder).
Yeast: I use active dry yeast, which needs to be hydrated before. You can use instant yeast (¾ of the amount given for active dry) and add it directly to the flour, then add the liquid; no need to foam it first. If using fresh yeast, the ratio is 3:1 to dry, and it is used the same way as the active-dry, where you need to hydrate it first and let it foam.
Milk: I like whole milk for its richness, but reduced-fat and lactose-free milk also work.
Flour: We use both all-purpose and cake flour. I find that a mix renders softer rolls. You can use only all-purpose flour if that's all you have.
Brown sugar: we use light, but dark also works.
Powdered sugar: also known as icing sugar or confectioners' sugar.

Light gray surface with bowls containing ingredients for chocolate cinnamon rolls.

Variations & substitutions

Orange zest: add a sprinkle to the chocolate filling. The combo of chocolate and orange is fantastic.
Nuts or raisins: sprinkling chopped nuts for crunch or raisins for chewiness and sweetness onto the chocolate filling.
Cream cheese frosting: go the traditional route with a non-chocolate finish. It will be less intense, but still excellent rolls!

How to Make Sure Yeast Works

Check expiration date: Replace if expired.
Visual check: Should be beige to light brown and granular/powdery. Avoid if grayish, clumpy, or discolored.
Smell test: Should have a mild, slightly sweet smell. Strong or unpleasant odors indicate it's bad.

Proofing test: Mix ½ teaspoon sugar in ¼ cup warm water (comfortable to touch). Sprinkle ½ teaspoon of dry yeast on top and stir gently. Wait 5-10 minutes until you start to see some activity. Fresh yeast will foam and bubble more; instant bubbles less than active dry yeast.

Golden Rule: When in doubt, buy new! It's better to be safe than to have your baked goods fall flat and be inedible.

Steps to make chocolate rolls

There is something about working with yeast that is irresistible to me. But I know it's not everyone's favorite subject. It takes a bit of work and organization. You have to adapt to its rhythm.

This dough is straightforward and quite easy to work with.

Organization: read the recipe first and ensure you have ingredients at the correct temperature, utensils and equipment needed, and enough workspace. This will make the process so much easier.

Glass bowl with sweet dough before rising. Light gray surface.

Sweet dough before rising for the first time: Use a large bowl and cover it loosely with plastic wrap or a clean kitchen towel.

Cinnamon roll dough doubled in size in a glass bowl on a light gray surface.

The dough will double, and that's your cue to know it's ready. It will feel much softer and easier to work with.

Buttering sheet of cinnamon rolls dough on beige parchment paper.

I like to use parchment paper to guide me with the size and shape of the rectangle. But you can use a marble countertop. Be careful when spreading the soft butter so you don't tear the dough.

Rolling chocolate filled rolls dough on beige parchment paper.

Sprinkle the cinnamon-chocolate mixture on top of the butter. Roll tightly from the long side.

Dark metal pan with chocolate rolls before rising. Top view.

Cut the dough into 12 pieces and use a buttered baking pan or tray that holds them comfortably before rising and a bit snugly after they puff for the last time.

Proofed chocolate cinnamon rolls in a dark baking pan.

The rolls must rise again before baking and will bump into each other.

Chocolate glaze

We forgo the traditional cream cheese frosting and use a dark chocolate ganache icing. The result is sweet and gooey. Plain irresistible.

Let the glaze cool down slightly and thicken before pouring it on room-temperature rolls. Don't pour it while the rolls are hot or warm, or it will melt too much.

Black metal baking tray with chocolate glazed rolls.

Overnight rolls

Once you know how yeast works and get some practice, you can pop the dough into the fridge until the next day or freeze the unbaked rolls in the pans and give them their last rise after returning to room temperature.

Important: do it in stages, first transfer the pan to the fridge and when it's thawed, transfer it to the counter so it comes to room temperature and starts its final rise.

This last step might take a few hours, depending on the room's temperature and how cold the rolls are.

Bitten chocolate cinnamon roll on a white plate.

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