Homemade Chocolate Cinnamon Rolls

Step 1

Pour warm milk into a large mixing bowl or bowl of a stand mixer. Add the 1 tsp of sugar and sprinkle the yeast over top. Whisk to combine and set aside for 5 minutes to allow the yeast to bloom. **see notes

Step 2

Once the yeast has bloomed, add in the eggs, granulated sugar, butter and salt. Mix until combined. Add in about 4 1/4 cups of flour and mix until combined.

Step 3

Change to your dough hook at this point and let the dough hook beat your dough on medium speed. Continue to add flour slowly until your left with a somewhat tacky dough. It should stick to your finger but not stay when you pull your finger away. (Like putting your finger against a piece of tape.

Step 4

Now you can continue to knead the dough with the dough hook or you can turn it onto the counter and knead by hand until the dough becomes smooth and passes the windowpane test. (Pull off a small piece of dough and stretch it while holding it up to the light. If you can see through it and it doesn't tear, your dough is ready)

Step 5

Place the dough into a well greased large bowl and cover with saran wrap or a tea towel. Place the dough in a warm area or proofing drawer for about an hour or until the dough doubles in size. I like to turn my oven on for just a minute to make it warm and allow my dough to proof in the slightly warmed oven.

Step 6

While the dough proofs, combine the brown sugar, cinnamon and cocoa powder and set aside.

Step 7

Once the dough has doubled in size, punch it down and turn it onto a clean, lightly floured surface. Roll out the dough into a rectangle, about a 1/4 inch thick. Should measure about 23 inches x 14 inches.

Step 8

Spread the softened butter on top of the rolled out dough, using your hand or spatula. I like to use my hand. Then sprinkle the cinnamon mixture over top. Then spread the chopped chocolate over top.

Step 9

Starting on the long end, roll the dough up tightly and as evenly as you can. Gently cut the messy ends of the log you've rolled and set these aside to fry later. (***see notes)

Step 10

Cut the log into 12 equal pieces, about 1 3/4 inch slices. Place the slices spiral side up in a lightly greased 9x13 or 10x15 baking pan. (****See notes for overnight instructions)

Step 11

Cover the pan with a tea towel or saran wrap and proof for another 30 minutes or until they've doubled in size. While they proof, preheat the oven to 375℉.

Step 12

Heat your whipping cream and pour over top of the rolls once they're proofed. Bake until the internal temperature measures 190℉/87℃, about 22-30 minutes. This will vary greatly depending on size of pan and if you're using glass vs. metal.

Step 13

While the rolls are cooking, add the butter and cream cheese to the bowl of a stand mixer or large mixing bowl. Beat until smooth. Add in the icing sugar, cocoa powder and vanilla and continue mixing until creamy and smooth, about 1 minute.

Step 14

Allow the cinnamon rolls to cool for about 10 minutes before frosting and enjoy!