For the filling:
1️⃣ While the dough rises, make the chocolate cinnamon roll filling. In a medium-sized bowl, mix together 2/3 cup packed light brown sugar, 2 tablespoons of black cocoa, and 1 teaspoon of ground cinnamon, then set aside. 🍂🍫

For the dough:
2️⃣ Preheat your oven to 200°F (95°C). 🔥

3️⃣ In a large bowl or the bowl of a stand mixer, combine 3 1/4 cups of flour, 1/2 cup unsweetened cocoa powder, 1 packet instant yeast (or about 2 teaspoons), 1 tsp instant coffee, and 1 tsp salt. 🥄

4️⃣ In a separate bowl, add 1 cup milk, 1/2 cup granulated sugar, and 1/4 cup softened butter into a microwave-safe bowl. Heat on high power for 60-90 seconds, until the mixture is warm to the touch. Stir to combine the ingredients. 🥛🍶

5️⃣ Slowly add the warm milk mixture into the flour mixture and mix on medium speed with a dough hook until the dough comes together. Add in one large egg and mix on a low speed until a sticky dough ball forms. 🍳

6️⃣ Continue to mix on medium speed for 2-3 minutes, until the dough becomes more elastic. As the dough mixes, add additional flour 1 tablespoon at a time until the dough begins to leave the sides of the bowl. The dough should feel tacky but not sticky. 🥣

7️⃣ Cover your bowl with plastic wrap and let the dough rest for 15 minutes. This allows the gluten in the dough to relax a bit, making it easier to roll out. 🌬️

8️⃣ Generously flour your counter and roll your dough ball into a large rectangle, 12 inches x 18 inches. It should be about 1/2 cm thick. Spread 1/4 cup of softened butter over the dough, leaving 1 inch on the long side of the rectangle uncovered. This will make it easier to seal the log once it’s rolled. 🧈

9️⃣ Sprinkle the chocolate cinnamon roll filling evenly over the buttered area, and pat down with the back of a spoon or spatula. 🍫🥄

🔟 Tightly roll the dough horizontally, toward the uncovered strip. Cut dough log into 9 equal pieces with dental floss (or more pieces if you want smaller/shorter cinnamon rolls), and place in a greased square pan (8in x 8in). 🔪

1️⃣1️⃣ Turn the oven off. Cover the cinnamon roll pan with foil and place in the oven for 30 minutes (or until the cinnamon rolls have risen). 🕒

1️⃣2️⃣ Remove the pan from the oven and take off the tinfoil. Turn the oven back on and heat to 350°F (175°C). 🔥

1️⃣3️⃣ Once the oven has preheated, bake for 26-32 minutes. I find the sweet spot in my oven is about 28 minutes. Bake time can vary based on how gooey or baked through you like your cinnamon rolls. ⏲️

For the glaze:
1️⃣4️⃣ To make the cinnamon roll frosting, place 1 tablespoon of unsalted butter, 2/3 cup milk or dark chocolate chips, and 3 tablespoons of whole milk in a medium-sized bowl. Heat in the microwave on medium-high heat (power level 7) for 60 seconds. 🥄

1️⃣5️⃣ Stir the mixture together with a spoon or whisk, making sure all the chocolate is melted. Add in 1 cup of powdered sugar and 1 teaspoon vanilla extract. Mix together until smooth. 🍫

1️⃣6️⃣ Let the cinnamon rolls cool for 5-10 minutes, then drizzle the chocolate glaze over the cinnamon rolls. Serve warm. 🍩🍫