Activate the Yeast: Whisk the warm milk, yeast, and granulated sugar together in the bowl of a stand mixer fitted with a dough hook or paddle attachment. Cover and let the mixture stand for 5 minutes.
Mix the Dough: Add the eggs, melted and slightly cooled butter, salt, and 1 cup of flour. Beat on low speed for 30 seconds, then scrape down the sides of the bowl with a silicone spatula. Add the remaining flour and beat on medium speed for about 2 minutes, until the dough comes together and begins pulling away from the sides of the bowl. If mixing by hand, use a large wooden spoon or silicone spatula. Knead the Dough: Continue beating the dough in the mixer for 5–7 full minutes, or knead it by hand on a lightly floured surface for the same amount of time. If it becomes excessively sticky, add flour 1 teaspoon at a time only as needed. The finished dough should remain soft and slightly tacky rather than dry. When gently poked, it should slowly bounce back; alternatively, check that a small piece passes the windowpane test without tearing. First Rise: Lightly grease a large bowl with oil or nonstick spray. Place the dough inside and turn it so all sides are lightly coated. Cover with aluminum foil, plastic wrap, or a clean kitchen towel and let rise in a relatively warm environment for 1–2 hours, or until doubled in size. Prepare the Bundt Pan: Generously grease a 10–12-cup Bundt pan with butter or nonstick spray, with nonstick spray being the preferred option for this recipe.
Prepare the Cinnamon-Sugar Coating: Melt ½ cup (113 g) of the unsalted butter in a medium bowl. In a separate medium bowl, combine the granulated sugar and ground cinnamon. Set aside the remaining butter, brown sugar, and vanilla extract for the later topping. Shape the Dough: Punch down the risen dough to release the air. Divide off small pieces one at a time and roll each into a ball about 1.25 inches in diameter. Make approximately 40–45 balls in total, keeping them relatively small. Dip each ball into the melted butter, then generously roll it in the cinnamon-sugar mixture. Arrange the coated dough balls in the prepared Bundt pan as you work. Rest the Shaped Bread: Cover the filled Bundt pan with aluminum foil, plastic wrap, or a clean kitchen towel. Let the shaped dough rest for 20 minutes, during which the balls should rise slightly.
Preheat the Oven: Move the oven rack to a lower position and preheat the oven to 350°F (177°C). Baking the monkey bread lower in the oven helps prevent the top from burning.
Finish the Brown-Sugar Coating: Melt the remaining ¼ cup (60 g; 4 tablespoons) butter. Whisk in the brown sugar and vanilla extract, then pour the mixture evenly over the shaped monkey bread.
Bake the Monkey Bread: Bake at 350°F (177°C) for 35–45 minutes, or until the top is golden brown. If the surface begins browning too quickly, loosely cover the pan with foil.
Cool and Invert: Allow the baked monkey bread to cool in the pan for 5–10 minutes. Carefully invert it onto a large serving plate or cake stand.
Make the Vanilla Icing: Whisk the confectioners’ sugar, whole milk, and vanilla extract together until combined and smooth.
Finish and Serve: Drizzle the vanilla icing over the monkey bread. Serve in generous slices or pull apart the individual gooey pieces for a fun, shareable presentation.
Store Leftovers: For the best flavor, serve the monkey bread the same day. Cover leftovers tightly and keep them at room temperature for 1 day or refrigerated for up to 4 days.
