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For the dough:
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In a small measuring cup, combine warm water, a pinch of the sugar and active dry yeast and allow to sit until foamy and activated about 5 minutes.
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In another glass measuring cup or small bowl, combine milk and butter and warm in the microwave for 30 seconds at a time until milk is warmed through and butter is melted
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In the bowl of your standing mixer fitted with the dough hook, mix 2 cups of the flour, sugar and salt and stir briefly to combine. Add the egg, milk and butter mixture, yeast mixture and vanilla and mix until it's all incorporated. Slowly add the remaining flour and continue to mix on low to medium speed until a smooth dough has formed, 5-7 minutes.
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Grease a large bowl with vegetable oil and set aside.
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Turn out the dough onto a floured surface and knead together briefly to form a ball. Place into the well oiled bowl, cover with plastic wrap and allow to rise in a warm spot until doubled in size, about 60-90 minutes. (Tip: To make ahead, place dough in the refrigerator and allow it to rest and rise overnight. The next day, take it out of the fridge about 30 minutes in advance to allow it to come to room temperature and then continue with the rest of the recipe.)
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For the cinnamon sugar mixture:
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Melt 2/3 of the butter in a microwave safe bowl, heating for 30 seconds at a time until melted.
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In another small bowl, combine granulated sugar and cinnamon and mix together. The vanilla, brown sugar and remaining 1/3 of the butter will be used for pouring over the bread before baking.
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Gently punch to deflate the dough. Generously spray a 10 cup bundt pan with cooking spray. (I used a 6 cup bundt pan but it was tight.) Pull off pieces of dough and roll into balls about an inch or larger. Dip each dough ball into the melted butter and then roll in the cinnamon and sugar. Arrange them evenly around the bundt pan. Continue to pinch off pieces of dough and coat them in the butter and cinnamon and sugar while you build layers. You may need to have extra sugar and cinnamon on hand for rolling, depending on how much you use to coat your dough balls.
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Cover with plastic wrap and let it sit in a warm place for another 30-45 minutes or until dough balls have risen and puffed up.
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Preheat your oven to 375 F.
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In a small saucepan, melt the remaining 1/3 of the butter. Once melted, remove from heat and whisk in brown sugar and vanilla extract. Pour over the dough balls.
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Bake in the preheated oven for 35-40 minutes or until golden brown and baked through (see note below). Remove from oven. Allow the monkey bread to rest in the pan for about 5 minutes before inverting it out of the pan onto a wire rack or plate.
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For the glaze:
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While the monkey bread is baking, prepare the cream cheese glaze. Place all the glaze ingredients except the milk in the bowl of a standing mixer and mix until combined. Add the warm milk by the tablespoon until you reach your desired consistency. I like my cream cheese glaze runny and easy to drizzle, so I use a tad more milk. Drizzle the cream cheese glaze over warm bread and serve.
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Note: If you want your bread to be more gooey, with more caramel, you can repeat the same process with an additional 1/4 cup melted butter, brown sugar and vanilla and pour it over inverted bread along with the cream cheese glaze and you have double the caramel goodness. It's up to you!
