In the bowl of a stand mixer, add the milk, yeast,
sugar and whisk slightly to combine.
Let sit for approximately. 5 minutes or until the yeast begins to foam and bubble.
Add in the melted butter, egg, and salt and whisk to combine.
Attach the knead hook to the mixer and add in 2 cups of flour.
Mix until well combined.
If the dough still sticks to the bowl, gradually add more flour about 2 tablespoons at a time until the dough does not stick to the sides or bottom of the bowl. It should be just slightly tacky but not come off on your fingers. Knead for an additional 4-5 minutes until you have an elastic dough. (NOTE: a good way to check is to remove a piece of dough and stretch between your thumbs and index fingers. If you can see through the dough without it ripping, it is ready)
Once the dough is ready, place into a large, lightly greased, bowl and cover with plastic wrap and set in a warm spot to rise for 30-45 minutes or until doubled in size.
I like to leave mine inside my oven so there are no drafts.
Prepare an 8x8 baking dish with non-stick spray and set aside.
Once the dough has risen, punch down and place out on a lightly floured surface and roll out into a rectangle about ¼” thick.
Smooth the softened butter over the entire surface of the dough.
Combine both sugars, cocoa, and cinnamon into a small bowl and whisk to combine. Sprinkle all over the butter and top with the chocolate chips.
Make sure chocolate chips are spread out as evenly as possible.
Starting from the small end, roll the dough tightly into a log and using a sharp bread knife, cut into 9 equal pieces and place in the prepared baking dish.
Cover with plastic wrap and set in a warm place for about 30 minutes or until doubled in size.
Preheat your oven to 350 degrees F.
Once your rolls have doubled in size, bake for 15-20 minutes or until the tops are golden brown.
Place the rolls on a wire rack to cool. Meanwhile, combine the butter and cream cheese into the bowl of a stand mixer and beat with a paddle attachment for 1-2 minutes.
Add in the powdered sugar and cocoa powder and mix on low speed until combined.
Add the heavy cream and mix on slow until combined then increase the speed to high and mix for 2-3 minutes or until you get a “whipped” consistency.
Pour the icing on the cinnamon rolls and smooth out evenly.
Enjoy every bite!