For the Dough:
1 cup whole milk
5 tablespoons unsalted butter
2½ teaspoons (1 packet) dry instant yeast
3 tablespoons granulated sugar
½ teaspoon kosher salt
4¾ cups all-purpose flour, divided, plus more for kneading and rolling
3 large eggs
½ teaspoon canola oil
For the Filling:
½ cup unsalted butter, softened, plus more for greasing
1½ cups packed light brown sugar
2 tablespoons all-purpose flour
1 tablespoon ground cinnamon
½ teaspoon kosher salt
For the Glaze:
⅔ cup granulated sugar
2 tablespoons light brown sugar
4 tablespoons unsalted butter
⅓ cup evaporated milk
1 teaspoon vanilla extract
Pinch kosher salt
1. Make the dough: In a small saucepan and over low heat, warm the milk and butter until the butter has melted and the temperature reaches 105° on a thermometer. Pour the mixture into the bowl of a stand mixer and sprinkle the yeast on top (do not stir it in). Let it sit until it foams, 8 to 10 minutes, then using a wooden spoon, stir in the sugar and salt. Add 2¼ cups of flour and stir until just combined, about 30 seconds. Add the eggs and stir until completely incorporated, scraping down the sides as needed, another 30 seconds. Transfer the bowl to the stand mixer fitted with a paddle attachment and beat on medium-high speed until a smooth batter forms, 2 to 3 minutes. Remove the bowl from the mixer and stir in the remaining 2½ cups of flour, mixing until the dough comes together and forms a tacky ball, 3 to 4 minutes.
2. Transfer the dough ball to a floured surface and knead until smooth and elastic, 3 to 4 minutes, adding more flour as needed if the dough is wet. Wipe the mixing bowl clean then coat it with the canola oil. Add the dough ball, turning once to grease the surface of the dough. Cover the bowl with plastic wrap and let the dough rise in a warm place until it doubles in size, 50 minutes to 1 hour.
3. While the dough is rising, make the filling: In a medium bowl, stir together all of the ingredients, forming a granular paste. Set aside.
4. Grease a 9-by-13-inch pan with butter and set aside. When the dough is ready, roll it out onto a floured surface into a 12-by-18-inch rectangle that's ⅛-inch thick. Spread the filling over the dough, leaving a 1-inch border on all sides. Starting at one long end, roll the dough into a log. Pinch to seal the long seam and place the log onto a lightly floured surface, seam-side down. Using a large serrated knife, cut the log into 15 pieces, each about 1½ inches thick, and place in the prepared pan, cut-side up. Loosely cover with plastic wrap and let sit in a warm place for a second rise until puffy and slightly warm to the touch, 20 to 25 minutes. Make ahead: The rolls can be refrigerated up to 1 day. To bake, remove the pan from the refrigerator and let the dough rise for 1 hour, then proceed with the recipe.
5. Meanwhile, position a rack in the center of the oven and preheat to 375°. After the second rise, remove the plastic cover and bake until golden brown, 18 to 22 minutes.
6. While the rolls are baking, make the glaze: In a small saucepan, combine the sugars, butter and evaporated milk, and place over medium heat. Cook, whisking constantly, until the butter is melted and the sugars have dissolved, 2 to 3 minutes. Remove from the heat and whisk in the vanilla and salt. Let cool and set aside.
7. Remove the cinnamon rolls from the oven and drizzle the glaze over top. Let cool at least 20 minutes before eating.