1. Activate the Yeast:

Begin by activating the yeast. In a small bowl, combine the warm milk and granulated sugar. Sprinkle the yeast over the top of the milk mixture and let it sit for about 5-10 minutes until it becomes foamy. This step ensures that the yeast is alive and ready to make your dough rise.

2. Mix the Wet Ingredients:

In a large mixing bowl, combine the melted butter, egg, and vanilla extract. Once the yeast mixture is foamy, add it to the wet ingredients and mix well. This will form the liquid base for your dough.

3. Combine the Dry Ingredients:

In a separate bowl, whisk together the flour and salt. Gradually add the dry ingredients to the wet mixture, stirring until a dough forms. It’s okay if the dough looks a little shaggy at first; you’ll knead it shortly to smooth it out.

4. Knead the Dough:

Turn the dough out onto a lightly floured surface and begin kneading. Use the palms of your hands to press down and fold the dough over itself. Keep kneading for about 5 minutes, or until the dough becomes smooth and elastic. If you have a stand mixer with a dough hook, you can use it for this step to save time and effort.

5. Let the Dough Rise:

Once the dough is kneaded, place it in a greased bowl. Cover the bowl with a clean kitchen towel and let it rise in a warm place for about 1 hour, or until it has doubled in size. This is when the yeast works its magic, creating air bubbles that will make the dough light and fluffy.

6. Make the Filling:

While the dough is rising, prepare the filling. In a small bowl, combine the softened butter, brown sugar, and cinnamon. Stir until the mixture is smooth and well-combined. This will create a sweet, buttery filling that will melt into the dough as the rolls bake.

7. Roll Out the Dough:

Once the dough has doubled in size, punch it down gently to release the air bubbles. Turn it out onto a floured surface and roll it into a large rectangle about 1/4 inch thick. Use a rolling pin to evenly spread the dough.

8. Spread the Filling:

Evenly spread the cinnamon-brown sugar mixture over the rolled-out dough. Be sure to cover the entire surface to ensure every bite has that sweet filling. Once the filling is spread, sprinkle the chocolate chips over the top. You can use semi-sweet or milk chocolate chips, depending on your preference.

9. Roll and Cut:

Starting from one long edge, tightly roll the dough into a log. Once it’s fully rolled, use a sharp knife to slice the log into 12 equal pieces. The rolls should be about 1 to 1 1/2 inches thick. Be gentle when cutting to ensure the rolls don’t lose their shape.

10. Place in Baking Dish:

Grease a 9×13-inch baking dish and arrange the rolls in the dish, leaving a little space between each one. Cover the dish with a kitchen towel and let the rolls rise for another 30 minutes. During this time, they will puff up and fill the dish, ready to bake.

11. Bake the Rolls:

Preheat your oven to 350°F (175°C). Once the rolls have risen, place the baking dish in the oven and bake for 25-30 minutes, or until the rolls are golden brown and cooked through. You’ll know they’re done when the tops are lightly golden, and the dough is firm to the touch.

12. Make the Frosting:

While the rolls are baking, prepare the frosting. In a mixing bowl, beat the softened cream cheese and butter until smooth. Gradually add the powdered sugar and vanilla extract, mixing until everything is well combined. If the frosting is too thick, add 1-2 tablespoons of milk until it reaches a spreadable consistency.

13. Frost and Serve:

Once the rolls are out of the oven, let them cool for a few minutes. Spread the frosting over the warm rolls, allowing it to melt into the crevices. Serve immediately while they’re still warm for the best flavor and texture.