Ingredients
- 1 cup whole milk
- ¼ cup vegetable oil
- 6 Tbsp (¼ cup + 2 Tbsp) granulated sugar
- 2 ¼ tsp yeast (1 packet)
- 2 ¾ cups all-purpose flour
- 1 tsp salt
- Orange food coloring
- Halloween sprinkles, optional
Chocolate Cinnamon Filling
- 6 Tbsp unsalted butter, softened
- ¾ cup packed dark brown sugar
- 3 Tbsp black cocoa
- 3 tsp ground cinnamon
- ½ tsp salt
- 2 tsp vanilla extract
- ½ cup dark chocolate chips* (optional)
Vanilla Icing
- 1 ½ cups confectioners’ sugar
- 3 Tbsp milk
- 1 tsp vanilla extract
Instructions
- Heat milk, vegetable oil, and sugar in a medium saucepan over medium heat, stirring occasionally, until it’s hot, but not at the point of boiling. It should be about 170-180 degrees.
- Pour milk mixture into the bowl of a stand mixer with paddle attachment (if you don’t have a stand mixer, you can do it by hand- see notes below) and let rest for about 10 minutes to cool a bit (you want it at about 110 degrees). Sprinkle yeast over the top of milk mixture. Let sit for 5 minutes.
- Add flour and salt to milk mixture and mix on low for 1 minute, until flour is incorporated. Switch to dough hook attachment and add orange food coloring to mixture. Knead on medium speed until dough is comes together and is smooth, 6-8 minutes.
- Transfer dough to a lightly greased mixing bowl, cover with a towel, and place in a warm location. Let dough rise for about an hour, until it doubles in size.
- Once dough has risen, punch it down and place on a lightly floured surface. Roll dough out into a rectangle, about 12×16 inches.
- Using a knife spread chocolate cinnamon filling over the entire dough rectangle, all the way to the edges. Sprinkle chocolate chips over the top, if using.
- Roll the dough lengthwise into a tight log, and use a sharp knife or unflavored dental floss to cut the log into 12 equal slices (about 1 ¼” thick). Arrange rolls in a pan 9×16 baking pan lightly sprayed with cooking oil or brushed with melted butter.
- Cover pan with a towel and place in a warm area to rise for about 45 minutes.
- When rolls are almost done rising, preheat oven to 350 degrees.
- Bake rolls for about 20-22 minutes, until cooked through and no longer doughy.
- Let cinnamon rolls rest for about 5 minutes before drizzling with vanilla icing and adding sprinkles, if desired.
Chocolate Cinnamon Filling
- Add all ingredients except chocolate chips to a medium bowl and use a wooden spoon or rubber spatula to combine.
Vanilla Icing
- Add all ingredients to a small bowl and whisk to combine.
Notes
- If you don’t have a stand mixer, put milk mixture in a large bowl and use a wooden spoon to combine, salt, and orange food coloring. Once dough comes together, place on a lightly floured surface and use your hands to knead dough for about 10 minutes.
- If you don’t have dark chocolate chips, you can use semisweet.
- I like King Arthur’s Black Cocoa Powder.
- See post body for tips on making portions of this recipe in advance.

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