Gooey chocolate cinnamon rolls! This delicious recipe for cinnamon buns is a twist on an old family classic, featuring a decadent filling made with dark chocolate and cinnamon. Baked to perfection and then drizzled with more chocolate glaze, these chocolate rolls make for a sinfully sweet breakfast or tasty treat.

These cinnamon rolls are so gooey and delicious, stuffed to the brim with chocolate cinnamon filling. This recipe makes a huge batch of them too, so they are perfect if you’re feeding a large crowd or if you want to freeze a bunch for later.

The glaze is also totally not necessary, either if you don’t like your rolls super sticky or because maybe you’re planning to freeze them in a ziplock bag. These cinnamon rolls are great with or without the glaze, though glazing cinnamon rolls is that secret trick that makes them super moist and gooey. Either way, these buns are a real treat!

There are a few steps to making perfect cinnamon buns, so let’s go over them:

• Use warm milk. Make sure the milk is heated to about 110˚F. I usually heat the milk in a saucepan on the stove until it is just about break into a simmer. About 1-2 minutes in the microwave also does the trick, just make sure to microwave the milk in smaller stints of about 30-45 seconds at a time.
• Bloom the yeast for 15 minutes with warm milk and sugar. The sugar and warm milk are the ultimate secret to great bloomed yeast. Mix these three ingredients together in a bowl, then cover the bowl with plastic wrap and a tea towel. Let it sit for 15 minutes to get nice and bubbly and bloomed.
• Knead the dough by hand for 3- 5 minutes. Knead the dough for 3-5 minutes by hand or using a spatula if it’s still a bit sticky. You can add up to an extra quarter cup of flour if the dough is too sticky, but error on the side of “less is more”.
• Please don’t use an electric mixer. Electric dough mixers can overwork the dough all too easily, and then you’ve wasted your perfectly bloomed yeast.
• Oil and cover your dough for the first rise. For for the first rise, make sure both the dough and the inside of the bowl are coated with a little olive oil, and that it is then covered with plastic wrap ( you can also add a tea towel for extra protection). You don’t want your precious dough to dry out.

• Let the dough rise twice: 1 hour in a warm place, then again for 30 minutes in the baking dish, before baking.
  • Rise #1 (room temp, 1 hour): Let the dough rise for 1 hour in a warm place. It should be rubbed with a little olive oil and covered in plastic wrap so it doesn’t dry out.
  • Rise #2 (room temp, 30 mins): Let the dough rise once more in the baking dishes, after it’s been rolled up, filled, and cut into buns. Make sure to give the buns enough space in the pan for this second rise (don’t place them too closely together).

A few more tips:

• Bake the cinnamon buns at 350˚F for 30 minutes. Being that this is a more delicate and cake-like dessert, an oven temperature of 350˚F is perfect. Make sure not to over bake them or they will get too dry. I usually start checking mine after 25 minutes.
• Store your cinnamon buns in an airtight container in the fridge or freezer. These buns keeps well in a sealed container in the fridge for about 7 days, or in the freezer for 2-3 months.

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Chocolate Cinnamon Rolls

Chocolate Glaze

• ¼ cup soft butter
• ¼ cup melted dark chocolate
• 1-2 cups powdered icing sugar
• 2 tbsp cocoa powder
• 1 tbsp cinnamon
• 2 tsp vanilla extract

Instructions

1. Add warm milk, yeast, and sugar to a bowl. Stir lightly, then let the mixture sit for 15 minutes until bubbly and frothy. 
2. Combine the proofed yeast mixture, soft butter, beaten eggs, 4 cups of flour, and the salt in a large mixing bowl. Stir all the ingredients together until a dough forms. Knead the dough for 3 – 5 minutes. If the dough is still sticky, add a few extra tablespoons of flour. Shape into a ball.
3. Rub the dough and the inside of the bowl with a little olive oil. Cover the bowl with plastic wrap. Let the dough rise in a warm room for 1 hour, until doubled in size.

4. Prepare the baking dishes (9 x 13” rectangle pans, or 9-10” diameter circular pans). Line them with baking parchment, then grease with 1-2 tablespoons of soft butter. Set aside.
5. Punch the dough down and transfer to a lightly floured surface. Roll out a rectangle shape (12 x 18”). 

6. Mix the filling in a separate heat-safe bowl. Melt the chocolate pieces by microwaving them for 30-60 seconds at a time, stirring in between each stint until fully melted. Alternatively, melt the chocolate in a heat safe bowl over a pot of boiling water until smooth (wearing oven mitt recommended). Once melted, stir in the sugars, cinnamon, and cocoa powder. Let cool for 1-2 mins.

7. Spread the filling evenly over the dough layer.
8. Starting with the longer 18” edge that’s closest to you, gently yet tightly roll the dough up (like rolling up a yoga mat or scroll of paper!). Pinch along the seam of the dough to seal the loose edge. 
9. Use a sharp knife to cut the dough into into approx. 22-24 slices, each about 1.5 inch wide.

10. Place the buns in the baking dishes, cover the with plastic wrap and let rise for another 30 minutes. 
11. Preheat the oven to 350° F. Bake the buns in the fully heated oven for 30-35 minutes. Once they are baked and golden brown, remove the buns from the oven.

12. To make the glaze, melt the chocolate and butter together in a heat safe bowl, either using the microwave or double boiler as described in step 4. Once melted, mix in cocoa powder, cinnamon and vanilla. Add icing sugar little by little, until the glaze reaches your desired thickness. Slather or drizzle the glaze over the freshly baked buns. Serve and enjoy!

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Family Favourite Chocolate Cinnamon Buns