Microwave in 30-second intervals until it reaches about 105-110 degrees F. If it gets too hot, let it sit on the counter for a few minutes to come down in temperature.
Add warm milk, granulated sugar, and yeast to the bowl of your stand mixer. Use a fork to lightly stir it all together. Let sit for 5 minutes for yeast to bloom.
Add molasses, eggs, ½ cup butter, and 1 teaspoon vanilla extract. Use the fork again to lightly beat the eggs.
Pour in flour and ½ teaspoon salt. With the dough hook attachment on your stand mixer, knead the flour into the liquid ingredients until combined.
Continue to knead with the dough hook for another 8-10 minutes, or until the dough forms a ball and pulls away from the sides of the bowl. If your dough is too sticky, you can add up to another ½ cup of flour in 2 tablespoon increments. The dough should feel a little sticky but shouldn't come off on your fingers when pinched.
Grease a clean bowl lightly with oil. Remove dough from the mixing bowl and place it in the greased bowl, turning to coat in oil on all sides.
Cover with a clean kitchen towel and set in a warm place to rise for about 10 minutes.
Preheat oven to 350 degrees F. Grease a 9x13 inch baking dish with nonstick spray. Please see the notes above the recipe if using a glass baking pan.
Filling
In a medium bowl, add brown sugar, 2 tablespoons cinnamon, ginger, and allspice. Stir to combine.
Lightly flour a clean surface and roll the dough out into a rectangle until it’s about ½-inch thick.
Spread the softened butter all over the dough and sprinkle the brown sugar mixture on top.
Working from the longer side of the rectangle, cut 12 2-inch strips out of the dough.
Roll each strip tightly into itself to create a cinnamon roll.
Place the rolls, swirl-side up, in the greased baking dish.
Cover with the same clean dish towel and allow to sit in a warm place for another 20 minutes.
Frosting
While waiting for the rolls to rest, clean the bowl of your stand mixer.
Beat together cream cheese and ¼ cup butter with the paddle attachment.
Add in powdered sugar, ½ teaspoon vanilla, ¼ teaspoon cinnamon, and ¼ teaspoon salt. Beat again until smooth and creamy.
Bake cinnamon rolls for 30-35 minutes, or until baked in the center and golden brown on top. Remove from the oven and let cool for about 10 minutes.
Spread frosting on top of warm rolls and decorate with holiday sprinkles, if using.
Notes
Whole milk: Whole milk makes for richer, softer dough. You can use milk with a different fat percentage, but it may result in a leaner dough.
Instant yeast: Instant yeast doesn't need to be proofed; however, briefly proofing the yeast ensures that you can see that your yeast has been properly activated.
Molasses: I don't recommend using blackstrap molasses in this recipe. The flavor can be bitter and overpowering. However, if you like the flavor of blackstrap molasses, feel free to use it.
Butter: You can substitute salted butter if you prefer.
Cream cheese: I recommend using either full-fat cream cheese or 1/3-less fat cream cheese for best flavor.