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Grease a medium bowl with cooking spray. In a large measuring glass add warm milk and sprinkle yeast on top. Let sit until foamy, about 5 minutes. In the bowl of a stand mixer fitted with the dough hook, mix flour, sugar, and salt. Add yeast mixture and eggs. Mix until dough starts to come together. Add softened butter, 1 tablespoon at a time, letting each piece incorporate into the dough before adding the next. Continue mixing dough on medium-high speed for about 5 minutes. Dough will be soft and smooth and a little sticky. Transfer dough to prepared bowl and cover with a kitchen towel. Let rise until doubled in size, about 1 ½ hours. Grease a large bundt pan with softened butter, making sure to coat all of the sides well, including the inner tube. Lightly dust a clean work surface with flour and dump dough out onto surface. Pat into a square that’s about ½” thick. Cut into 60 equal pieces and roll into a ball that’s about 1” in size. In a small bowl, combine sugar and cinnamon. Place melted butter in another small bowl. Working one at a time, dip dough into butter, letting excess drip off, then roll in cinnamon sugar. Place into prepared bundt pan, layering as you go. Cover with a towel and let rise until dough has clearly expanded, 30 to 45 minutes. Preheat oven to 350°. Bake until top is deeply golden, about 40 minutes. Let cool 10 minutes, then invert onto a serving platter. Let cool 10 minutes more before icing. In a medium bowl, combine powdered sugar, cream, and vanilla. Spoon over still warm monkey bread.
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