Step 1: Prepare the Dough

1. In a large mixing bowl, combine 2 ¼ teaspoons of active dry yeast, ¼ cup of warm milk, and 1 tablespoon of sugar. Stir and let the mixture sit for 5-10 minutes until it becomes frothy. This ensures the yeast is activated.
2. In the meantime, whisk together 4 cups of flour, the remaining sugar, and ½ teaspoon of salt in a separate bowl.
3. Once the yeast mixture is bubbly, add the remaining warm milk, melted butter, eggs, and vanilla extract. Stir to combine.
4. Gradually add the flour mixture into the wet ingredients, stirring with a wooden spoon or dough hook attachment of a stand mixer. Mix until a soft dough forms.
5. Knead the dough on a lightly floured surface for about 5-7 minutes until it becomes smooth and elastic. If you’re using a stand mixer, knead the dough with the dough hook on medium speed for about 5 minutes.
6. Place the dough in a greased bowl, cover with a clean towel or plastic wrap, and let it rise in a warm place for 1-1.5 hours or until it has doubled in size.

Step 2: Make the Cherry Filling

While the dough is rising, prepare the homemade cherry filling.

1. In a medium saucepan, combine 2 cups of pitted cherries, ¼ cup of granulated sugar, 2 tablespoons of cornstarch, 1 tablespoon of lemon juice, and 1 tablespoon of water.
2. Cook over medium heat, stirring frequently, until the cherries begin to break down and the mixture thickens, about 5-7 minutes. If you’re using frozen cherries, make sure to thaw and drain them before cooking.
3. Once the filling has thickened, remove it from the heat and stir in 1 teaspoon of vanilla extract.
4. Let the cherry filling cool to room temperature while the dough finishes rising.

Step 3: Make the Cinnamon Sugar Filling

In a small bowl, combine ½ cup of brown sugar and 1 tablespoon of ground cinnamon. Set this mixture aside. This classic cinnamon sugar layer will add warmth and depth to the rolls, perfectly balancing the sweetness of the cherries.

Step 4: Roll Out the Dough

1. Once the dough has doubled in size, punch it down to release the air.
2. Roll the dough out on a lightly floured surface into a large rectangle, approximately 12×18 inches in size.
3. Spread ¼ cup of softened butter evenly over the dough, leaving a small border around the edges.
4. Sprinkle the cinnamon sugar mixture evenly over the buttered dough, followed by the cooled cherry filling.

Step 5: Roll and Slice the Dough

1. Starting from one of the longer sides of the rectangle, roll the dough tightly into a log.
2. Once rolled, use a sharp knife or unflavored dental floss to cut the log into 12 equal slices.
3. Arrange the slices in a greased 9×13-inch baking dish, making sure they have some space to expand during the second rise.
4. Cover the baking dish with a clean towel or plastic wrap, and let the rolls rise for another 30-45 minutes in a warm place until they are puffy and nearly doubled in size.

Step 6: Bake the Cherry Cinnamon Rolls

Preheat your oven to 350°F (175°C).

1. Once the rolls have finished their second rise, place the baking dish in the oven and bake for 25-30 minutes, or until the rolls are golden brown and baked through. If the tops start to brown too quickly, you can cover them with aluminum foil during the last 10 minutes of baking.
2. Remove the rolls from the oven and allow them to cool for about 10 minutes before adding the icing.

Step 7: Make the Icing

While the rolls are cooling, prepare the icing.

1. In a small bowl, whisk together 1 cup of powdered sugar, 2 tablespoons of milk, and ½ teaspoon of vanilla extract until smooth. If you prefer a tangier icing, add 1 tablespoon of cream cheese.
2. Drizzle the icing over the slightly warm rolls, allowing it to seep into the layers.

Step 8: Serve and Enjoy

Once the icing has been drizzled over the rolls, they are ready to be enjoyed! Serve them warm for the best experience—the soft dough, gooey cherry filling, and sweet cinnamon layers create the perfect bite every time.