Chocolate Cinnamon Rolls
Soft cinnamon rolls with a cocoa-cinnamon filling and melty chocolate chips, finished with chocolate cream cheese frosting.
- Total time
- 2 hr 41 min
- Bake
- 26 min
- Yield
- 12 rolls
- Level
- intermediate
The quick answer
Chocolate cinnamon rolls fold cocoa powder and chocolate chips into the cinnamon-sugar filling. Use Dutch-process cocoa for deep color and mini chips so they melt evenly without weighing down the swirl.
This is what happens when cinnamon rolls fall for a brownie. The tender enriched dough stays classic, but the filling turns rich and dark with cocoa, brown sugar, and just enough cinnamon to keep it in the family — then a handful of chocolate chips melts into gooey pockets as they bake. A silky chocolate cream cheese frosting takes them fully over the top. They're for the mornings when only chocolate will do.
Ingredients
Dough
- 1 cupwarm whole milk (about 110°F) — warm, not hot
- 2¼ tspinstant yeast — one packet
- ¼ cupgranulated sugar
- ⅓ cupunsalted butter, melted — cooled slightly
- 1 egglarge egg + 1 yolk — room temperature
- 4 cupsall-purpose flour — plus more to dust
- 1 tspfine salt
Chocolate filling
- ½ cupunsalted butter, very soft
- ¾ cuppacked brown sugar
- ¼ cupDutch-process cocoa powder
- 1 tbspground cinnamon
- ¾ cupmini semisweet chocolate chips
- ¼ tspfine salt
Chocolate cream cheese frosting
- 4 ozcream cheese, softened
- ¼ cupunsalted butter, softened
- 1 cuppowdered sugar
- 2 tbspcocoa powder
- 1 tspvanilla extract
- pinch of salt
Instructions
Whisk warm milk, yeast, and 1 tsp of the sugar. Let it sit until foamy.
Surface looks foamy and smells yeasty.
Add remaining sugar, melted butter, egg and yolk. Mix in flour and salt, then knead until smooth and elastic.
Dough is smooth, tacky but not sticky.
Cover and let rise in a warm spot until doubled.
Dough has doubled in size.
Stir the soft butter with brown sugar, cocoa, cinnamon, and salt into a spreadable paste. Roll the dough into a 16x12-inch rectangle and spread the cocoa filling to the edges, then scatter the chocolate chips.
Roll up tightly from the long edge, cut into 12 even rolls, and arrange in a buttered 9x13 dish.
Cover and proof until puffy and touching.
Rolls look pillowy and have filled the pan.
Bake at 350°F until set in the center; the cocoa makes color harder to judge, so watch the timer and the edges.
Edges are firm and puffed; center roll reads about 190°F.
Beat the frosting ingredients until smooth and spread over the rolls while they're warm.
Frosting glides and partially melts into the tops.
Make ahead, store & reheat
- Make ahead
- Assemble through cutting and arranging in the pan, cover tightly, and refrigerate overnight. Let sit at room temperature 45–60 minutes before baking.
- Storage
- Store covered at room temperature up to 2 days, or refrigerate up to 5 days.
- Reheating
- Microwave a single roll 15–20 seconds to re-melt the chocolate, or warm the covered pan at 300°F for about 10 minutes.
- Freezing
- Freeze baked, unfrosted rolls up to 2 months. Thaw, warm, then frost.
Substitutions
- Natural cocoa powder (slightly more acidic, still works) instead of Dutch-process cocoa powder
- Chopped dark chocolate instead of mini semisweet chocolate chips
Troubleshooting
- Hard to tell when they're done
- Cocoa masks browning, so rely on an internal temp of about 190°F and firm, set edges rather than color alone.
- Filling felt dry or grainy
- Make sure the butter is very soft so the cocoa and sugar blend into a smooth, spreadable paste before rolling.
Tools I reach for
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- Stand Mixer with Dough HookKneads enriched dough hands-free until smooth and elastic.
- Digital Kitchen ScaleWeighing flour is the single biggest fix for dry or dense rolls.
- Rolling PinRolls the dough into an even rectangle for tidy spirals.
- 9x13 Baking DishThe classic pan for a soft-sided pull-apart batch of rolls.
- Saigon (Vietnamese) CinnamonThe boldest, sweetest cinnamon for a deep filling flavor.
Frequently asked questions
- Dutch-process or natural cocoa?
- Dutch-process gives the deepest color and smoothest flavor, but natural cocoa works fine — the rolls just taste a bit sharper.
- Will the chocolate chips make them too sweet?
- Use semisweet or dark chips to balance the sugar. Mini chips distribute better and keep each bite from being overly rich.
- Can I skip the cinnamon?
- You can, but even a small amount rounds out the chocolate. For a pure chocolate roll, cut it to a teaspoon rather than removing it entirely.
Nutrition (estimate): 1 roll (of 12) · ~470 kcal. Nutrition is an automated estimate and will vary with brands and exact quantities.
Food safety: don't taste dough containing raw flour or raw egg. Refrigerate anything with cream cheese frosting, and reheat leftovers until piping hot.
Frostings & glazes to pair
Helpful guides
- The Best Cinnamon for Cinnamon Rolls (Saigon vs Ceylon)Which cinnamon makes the best cinnamon rolls — Saigon vs Ceylon vs Cassia, how strong each tastes, how much to use, and which to buy for a bold, warm swirl.
- Why Are My Cinnamon Rolls Dry? (And How to Fix It)The real reasons cinnamon rolls turn out dry — over-baking, too much flour, and over-proofing — plus exactly how to fix each one.
- How to Reheat Cinnamon RollsThe best ways to reheat cinnamon rolls — microwave, oven, and air fryer — with exact times and temperatures so they taste freshly baked.
More cinnamon rolls to try
- Classic Homemade Cinnamon RollsSoft, fluffy, bakery-style cinnamon rolls from scratch with a gooey brown-sugar filling and cream cheese frosting.
- Brioche Cinnamon RollsUltra-rich cinnamon rolls made from a buttery, high-egg brioche dough for an impossibly tender, feathery crumb.
- Apple Cinnamon RollsSoft cinnamon rolls stuffed with diced, cinnamon-spiced apples that bake down into little pockets of warm apple pie.
- Banana Bread Cinnamon RollsSoft cinnamon rolls that taste like banana bread — ripe mashed banana in the dough, a brown-sugar-walnut filling, and a tangy cream cheese frosting.
- Biscoff Cinnamon RollsCinnamon rolls loaded with Biscoff cookie butter in the swirl and a Biscoff glaze on top, finished with crushed Lotus cookies for caramelized, spiced-cookie flavor.
- Cheesecake Cinnamon RollsCinnamon rolls with a sweet cheesecake filling swirled in alongside the cinnamon sugar, so every roll bakes up with pockets of rich, tangy cheesecake.
- Red Velvet Cinnamon RollsStriking red cocoa-kissed cinnamon rolls with a soft, tender crumb and tangy cream cheese frosting — red velvet cake in pull-apart roll form.