Prepare the dough. Add the flour, yeast, and sugar to a mixing bowl and whisk to combine. Set aside.
Add the milk, butter, and vanilla extract to a small saucepan. Place the saucepan on the stovetop over medium heat and stir until the butter is fully melted. Do not allow the mixture to boil - remove it from the heat as soon as the butter is melted.
Add the dry ingredients, wet ingredients, and egg to the bowl of an electric stand mixer that is fitted with the dough hook attachment (or you can do this by hand).
Mix on low speed until the dough comes together and sticks to itself on the dough hook, and continue mixing for a few more minutes to knead the dough. You can also take the dough out of the bowl and knead by hand, but I prefer the mixer method.
Form the dough into a large ball and place it in a large, lightly greased bowl. Cover the bowl tightly with plastic wrap and place it in a warm spot to rise for at least 30 minutes. I like to put my dough in the oven with the light on but the heat turned OFF.
To prepare the filling, add the brown sugar, granulated sugar, cocoa powder, and cinnamon to a mixing bowl and whisk until fully combined. Set aside.
Turn the risen dough out onto a floured surface, create a small well in the center of the dough, and add the mini chocolate chips to the well. Fold and knead the dough until the chocolate chips are evenly distributed throughout the dough.
Roll the dough out until it is a roughly 10-inch by 14-inch rectangle.
Spread the softened butter onto the dough and sprinkle the cinnamon filling evenly over the butter. You may have some filling left over.
Starting with one of the long sides, roll the dough up tightly to form a long log shape, keeping it seam-side down.
Using a large serrated knife in a sawing motion, slice the dough into 12 even slices (I like to use unflavored dental floss to cut my cinnamon rolls).
Place the cinnamon rolls, evenly spaced, in a greased 9x13 inch baking dish.
Cover the baking dish tightly with plastic wrap and place it in a warm spot for at least 1 hour to allow the cinnamon rolls to rise.
Make the Browned Butter
Prepare the brown butter while the cinnamon rolls are rising. Place the stick of butter in a medium saucepan.
Place the saucepan on the stovetop over medium heat and cook the butter until it is dark brown and has a noticeable “caramel” smell. Make sure to stir the melted butter every few minutes, scraping up the brown bits from the bottom of the pan.
Pour the hot brown butter into a ramekin or small bowl and place it in the refrigerator until it is solidified, but still soft.
Bake the Cinnamon Rolls
Preheat your oven to 350 degrees Fahrenheit.
Remove the plastic wrap from the risen cinnamon rolls and bake them in the preheated oven for 30 minutes, or until the tops are golden brown (if they brown too quickly, loosely tent with foil for the last 10 minutes). Remove them from the oven and allow them to cool while you prepare the frosting.
Frost the Cinnamon Rolls
Prepare the frosting. Add the brown butter, powdered sugar, and half-and-half to a large mixing bowl and beat with an electric mixer until smooth and fluffy. Scrape down the sides of the mixing bowl with a rubber spatula and mix once more to ensure all the ingredients are fully incorporated.
Spread the frosting onto the still-warm cinnamon rolls and top with extra mini chocolate chips.
Serve warm, and store any leftovers covered with plastic wrap for up to three days.
Notes
How to Store: Cover leftover cinnamon rolls with plastic wrap or store in an airtight container for up to 2-3 days.
Tips:
Use room temperature ingredients for best results. Cold eggs or milk can slow down the yeast activation, so make sure everything is at room temp before mixing for a fluffier, more consistent dough.
Slice the rolls with unflavored dental floss for cleaner cuts. Instead of a knife, use dental floss to cut the rolled dough into slices—just loop it under the roll, cross the ends over the top, and pull tight. It prevents squishing and gives you neat, even rolls.
Let the brown butter cool completely before making the frosting. If it’s too warm, it’ll melt the powdered sugar and your frosting won’t whip up properly. Soft but solid brown butter creates that creamy, fluffy texture you want.