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Proof the yeast in the milk until the yeast is fragrant and bubbly, this takes a few minutes.
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In the bowl of a stand mixer, mix the melted butter, sugar, vanilla extract, and eggs together. Add the milk to the bowl and mix again.
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Add 4 Cups of flour to the bowl and mix well. Scrape down the bowl, and add the remaining flour. Mix well to combine all the ingredients, about 4-5 minutes
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Remove the dough to a well greased bowl. Cover with plastic wrap and let raise for at least 1 hour.
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When ready to assemble the monkey bread, preheat the oven to 350 degrees.
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Butter a large Bundt pan or tube pan.
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Combine the granulated sugar and cinnamon together in a bowl.
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Roll out the dough on a well-floured, clean, level work surface. The dough should be 1/2" thick. Cut into 1" x 1" pieces.
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Roll the pieces into the cinnamon and sugar mixture. Place a layer of pieces into the buttered pan. Sprinkle with brown sugar. Repeat with another layer of pieces, then sprinkle with more sugar. Repeat until the pieces and sugar are gone.
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Pour the melted butter over the pieces. Run a knife around the sides and central tube of the pan to help the butter get around the pieces.
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Bake for 33-37 minutes, until the top the golden brown.
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Run a knife around the sides and center tube. Flip out onto a large serving dish. Enjoy!