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Step 1
Let 2 large eggs sit at room temperature at least 30 minutes.
Step 2
Place 1 packet rapid-rise yeast and 1 tablespoon of the brown sugar in the bowl of a stand mixer fitted with the whisk attachment. Slowly pour in 1/4 cup warm water and stir to combine. Let sit until the yeast begins to activate and is foamy, about 10 minutes. Meanwhile, heat 4 tablespoons unsalted butter and 1 1/4 cups milk in a small saucepan over medium-low heat just until the butter is melted. Remove from the heat and let cool until warm to the touch.
Step 3
Add the butter-milk mixture to the yeast and mix on low speed until combined. Add the eggs one at a time and continue mixing until combined. Add 1/4 cup molasses and mix until combined.
Step 4
Place the remaining 1/2 cup packed brown sugar, 5 cups all-purpose flour, 1 teaspoon ground cinnamon, 1/2 teaspoon kosher salt, 1/2 teaspoon ground nutmeg, 1/4 teaspoon ground ginger, 1/4 teaspoon ground cloves, and 1/8 teaspoon ground allspice in a large bowl and whisk to combine. Add to the wet ingredients and mix on low speed until well combined and the dough begins to form a ball.
Step 5
Switch the whisk attachment to the dough hook. Knead on medium-high speed until the dough ball becomes smooth, elastic, and springs back when lightly pressed with 2 fingers, 5 to 7 minutes. If dough is too sticky, add more all-purpose flour 1 tablespoon at a time as needed.
Step 6
Lightly coat a large bowl with olive oil. Transfer the dough to the bowl, turn to coat, and cover with plastic wrap. Let rise in a warm place until doubled in size, about 1 hour.
Step 7
Place 1/2 cup packed brown sugar and 1 teaspoon ground cinnamon in a small bowl and stir to combine. Line a 9x13-inch baking dish with parchment paper or coat with butter.
Step 8
Melt 3 tablespoons unsalted butter in the microwave or on the stovetop. Transfer the dough to a floured work surface. Using a rolling pin, roll the dough out into a 9x14-inch rectangle that’s about 1/2-inch thick, with a long side closer to you.
Step 9
Lightly brush the dough with melted butter. Spoon the cinnamon-sugar mixture over the butter, then use the brush to sweep the sugar mixture evenly across the dough to ensure that every bite is sweet. Starting at the bottom, roll the dough tightly up into a log. Cut the log crosswise into 12 rolls. Transfer to the baking dish cut-side up in a single layer. Brush the tops of rolls with the remaining melted butter.
Step 10
Cover the baking dish and let the rolls rise until puffed and doubled in size, about 20 minutes. Meanwhile, arrange a rack in the middle of the oven and heat the oven to 375ºF. Place 4 ounces cream cheese and 2 tablespoons unsalted butter for the glaze in the bowl of a stand mixer (or large bowl if using an electric hand mixer) and let sit at room temperature to soften.
Step 11
Uncover the rolls and bake until a knife inserted into the center of the rolls comes out clean and the tops are golden brown, 35 to 40 minutes. Meanwhile, make the glaze.
Step 12
Bring 1/4 cup maple syrup to a boil in a small saucepan over medium-high heat. Remove from the heat.
Step 13
Beat the cream cheese and butter together with the paddle attachment on medium-high speed until fluffy, 2 to 3 minutes. Sift in 3 cups powdered sugar, then add the maple syrup, 1 teaspoon vanilla extract, and 1 tablespoon heavy cream. Mix on medium speed until smooth, 1 to 2 minutes. Add more heavy cream (1 tablespoon at a time if too thick) or powdered sugar (1 tablespoon at a time to thicken) if needed.
Step 14
When the rolls are ready, place the baking dish on a wire rack. Immediately spread half of the glaze over the rolls and let it melt, then cover and refrigerate the remaining glaze. Let the rolls cool completely, 15 to 20 minutes. Spread the remaining glaze evenly over the rolls before serving.