Ooey Gooey Chocolate Cinnamon Rolls

Make the cinnamon rolls. Add the warm milk and yeast to a large bowl. Set aside until the yeast has bloomed– about 5 minutes.

Next, add the brown sugar, egg, melted butter, and vanilla. Whisk to combine.

Using a stand mixer, on low-medium speed with the dough hook attachment, slowly stir the flour, cocoa powder, and salt into the wet ingredients. Once all of the flour has been added and a shaggy dough has formed, knead for 2-3 minutes or until the dough is smooth and elastic (it should bounce back when you poke it).

Transfer the dough to a lightly oiled bowl and cover it with plastic wrap and a tea towel. Place it in a warm place to rise until doubled in size — about 1-1.5 hours.

To make the filling, add the butter, brown sugar, and cocoa powder to a small bowl and stir to form a paste.

Assemble the sweet rolls. Once the dough has risen for 1 to 1.5 hours, turn it out onto a lightly floured surface.

Roll it into a rectangle that is approximately 18” long, 12” wide, and 1/4” thick.

Spread the butter mixture evenly across the top. Then roll into a tight log, starting at one of the long sides. For larger rolls, roll the tight log starting at one of the short sides.

Slice the log into 1” rolls. This will yield about 12 rolls, depending on how tightly you roll your log and whether you start rolling at a long or short side of the dough.

Butter a 9×13-inch baking dish or line it with parchment paper. Add the rolls to the dish, making sure they just barely touch. Depending on how tightly you rolled the dough into the log, you can either place rolls 3×4 OR 2×4 with extra rolls in another baking dish.

If you’re making the rolls in advance, wrap them in plastic and place them in the fridge for up to 12 hours. Bring the rolls to room temperature (about 30 minutes) when you’re ready to bake, and then skip to step 13.

If you aren’t making the rolls in advance, cover with plastic wrap and then a tea towel, and place them in a warm spot to rise until the rolls begin to touch — about 30 minutes. While the rolls rise, preheat your oven to 350°F.

Bake the chocolate sweet rolls for 18-22 minutes (depending on your oven) or until the centers are set; be sure not to overbake.

Allow the rolls to cool for 10 minutes before frosting.

To make the frosting, add the butter and cream cheese to a large mixing bowl. Using an electric mixer, beat until smooth and combined.

Add the powdered sugar, vanilla, and espresso powder and mix until combined. If the frosting is too thick, add milk 1 tablespoon at a time until you reach your desired consistency.