In the bowl of a stand mixer, combine 1 ½ cups lukewarm milk, 2 teaspoons of the sugar, and 1 ½ teaspoons instant yeast. Whisk together and let sit for 10 minutes, until the mixture looks foamy.

Add the remaining sugar, eggs, bread flour, butter, and salt to the bowl. Using the dough hook attachment, mix on medium speed for 6–7 minutes, until the dough is smooth, elastic, and slightly tacky but pulls away from the sides of the bowl.

Transfer the dough to a lightly oiled bowl, turning once to coat. Cover and let rise at room temperature for 1 hour.

After 1 hour, perform one stretch and fold (lift one side of the dough and fold it over itself, repeating on all four sides). Cover again.

Place the covered dough in the refrigerator and chill for 2 hours or up to 12 hours overnight. This cold proof develops flavor and makes the dough easier to work with when rolling out.

In the bowl of a stand mixer fitted with the paddle attachment, or in a mixing bowl with an electric hand mixer, cream together 1 cup packed brown sugar, 2 tablespoons ground cinnamon, and ¾ cup unsalted butter on medium speed until smooth and well combined. Set aside.

Lightly flour a clean work surface. Roll the chilled dough into a large rectangle, about 12x16 inches in size. Try to keep the edges as even as possible so the rolls bake uniformly.

Spread the filling mixture evenly over the dough, using an offset spatula or the back of a spoon to get it all the way to the edges. Leave about ½ inch of dough bare on one long side to help seal the log.

Starting with the opposite long side, roll the dough up tightly into a log. Roll slowly and evenly so the spiral stays tight and consistent all the way through.

Trim the uneven ends if needed. Use a very sharp knife or unflavored dental floss to cut the log into 12 equal pieces, each about 1⅓ inches thick.

Line a 9x13 baking pan with parchment paper, leaving an overhang on the long sides for easy lifting later. Lightly spray the sides of the pan with nonstick cooking spray.

Arrange the rolls cut-side up in the prepared pan, 3 across and 4 down. They should have a little space between them — they’ll puff and rise into each other during proofing and baking.

Cover the pan loosely with plastic wrap or a clean kitchen towel and let the rolls rise for 45–60 minutes, or until puffy and nearly doubled in size.

Once the rolls have finished their second rise, preheat the oven to 375°F.

Warm ½ cup heavy whipping cream just until it loses its chill (microwave for about 15–20 seconds). Gently pour the cream evenly over the tops of the risen rolls, letting it soak down into the layers.

Place the pan in the oven and bake at 375°F for 10 minutes. After 10 minutes, reduce the oven temperature to 350°F and continue baking for 20-25 minutes, until the rolls are deep golden brown on top.

If the rolls begin to brown too quickly, loosely tent the pan with foil during the last 10 minutes of baking.

Remove the pan from the oven and let the rolls cool for at least 20 minutes before frosting and adding toppings.

While the rolls are cooling making the brown sugar buttercream and the streusel.

Keep your oven to 350°F. Line a sheet pan with parchment paper.

In a medium bowl, whisk together the flour, brown sugar, granulated sugar, cinnamon, and salt.

Pour in the cooled melted butter and mix with a fork or spatula until clumps form. You want crumbly clusters, not dough. If it looks too sandy, squeeze some together with your hands.

Spread evenly on the prepared pan and bake for 8–10 minutes, until golden and set.

Let cool completely, then break into large pieces.

In the bowl of a stand mixer fitted with the paddle attachment, combine softened cream cheese, softened unsalted butter, and dark brown sugar. Beat on medium-high speed for 5 minutes, scraping down the sides of the bowl as needed. This step is important to dissolve the brown sugar and create a smooth base for the frosting.

Reduce the speed to low and gradually add the powdered sugar and milk or cream mixing until combined.

Add 1 teaspoon vanilla extract, then increase the speed to medium and beat for 1–2 more minutes, until the frosting is light and fluffy.

Once the cinnamon rolls have cooled slightly, spread the brown sugar buttercream evenly over the tops of the rolls.

Drizzle the dulce de leche straight from the jar or can over the frosted rolls. You can use a spoon or piping bag. I used the squeeze bottle it came in!

Generously sprinkle the prepared streusel crumble evenly on top. Serve warm or at room temperature.