This recipe requires a stand mixer.
In a small bowl, combine 2 ½ teaspoons of instant dry yeast with 1 cup of warm milk (115°F). Let it sit for about 5-10 minutes until it bubbles and becomes frothy.
Place the yeast mixture in the bowl of your stand mixer.
Add 2 large room-temperature eggs, vanilla, ½ cup of granulated sugar, and 8 tablespoons of softened salted butter to the yeast mixture. Mix until well combined.
Gradually mix in 4 cups of bread flour and 1 teaspoon of kosher salt. Stir the mixture until it forms a rough dough. Let it sit for 5 minutes.
Use the dough hook attachment and knead the dough on medium speed for about 5-7 minutes. The dough should be elastic and smooth. If the dough is way too sticky, add up to an additional ½ cup of flour (a little at a time) until it pulls away from the sides of the bowl. It’s okay if the dough remains slightly tacky and sticks to the bottom of the bowl, as this is preferable to being too dry.
Try not to add extra flour, as it can make the rolls dense and bready instead of soft and fluffy.
Place the dough in a lightly oiled bowl, cover it, and let it rise in a warm place for about 30-50 minutes, or until doubled in size.
While the dough is rising, beat together the filling ingredients until smooth (keep the chocolate chips off to the side until ready to assemble)
Flour your work surface. Sprinkle the top of the dough with a little more flour. Don't add a ton of flour! Roll the dough into a rectangle, about 22x14 inches.
Evenly spread the chocolate cinnamon filling over the entire surface of the dough. Sprinkle the chocolate chips evenly over the filling.
Starting from the long side, roll the dough tightly. Slice the dough into 12 equal pieces and place them in a parchment lined 9x13-inch baking pan. I used unflavored dental floss for clean cuts.
Cover the pan and let the rolls rise in a warm place for 20-30 minutes while you preheat the oven to 375°F.
Warm ½ cup of heavy cream until it’s just warm to the touch (not hot). Once the rolls have risen, pour the cream over the top, allowing it to soak in and around the rolls.
Position it on the center rack of the oven to ensure even baking, avoiding placement too close to the top or bottom. Bake the rolls in the oven for 20-25 minutes, until they are lightly golden and cooked through in the center. You can check with a toothpick. Check at 20 minutes, if they are getting too brown, cover with foil.
Let cool and top evenly with cream cheese icing. I recommend microwaving them for 10-15 seconds before enjoying for that melty cinnamon roll experience!