1 Make the dough: Whisk the warmed milk with the yeast and 2 tablespoons of the sugar in a measuring cup. Set it to the side to become foamy.
In the bowl of a stand mixer fitted with the dough hook, whisk together the remaining sugar, flour, salt, 3 tablespoons of melted butter. Add the yeast-milk mixture. Mix on low speed until a shaggy dough forms, then turn the mixer up to medium-low and knead for 10 minutes (set a timer!). When done, the dough should form a ball and spring back when you poke it.
2 Let the dough rise for one hour, or overnight: Gather the dough into a ball with your hands and place into a greased bowl. Cover well with plastic wrap. Let the dough rise on the counter for 1 hour, until doubled in size, or place in the fridge to rise overnight. (The dough may not quite double in size if you’re refrigerating overnight, but it should look risen and puffed.)
3 Make the apples while the dough rises (or before assembling, if you’ve chilled the dough overnight): Melt the butter for the apples in a medium skillet. Add the diced apples, cinnamon, and a pinch of salt. Cook over medium heat for about five minutes until the apples are just tender. Remove from the heat and set aside to cool. (The apples can be made up to a day ahead and kept refrigerated.)
4 Make the caramel sauce: In a large saucepan, combine the sugar and 1/2 cup of the apple cider, and stir over low heat until the sugar has dissolved. Once the sugar has dissolved, stop stirring, increase the heat to medium-low, and bring the mixture to a boil.
Continue to boil (without stirring!) until the sugar turns a deep golden caramel color, 320F to 330F. Remove from the heat and stir in the butter, followed by the salt, cream, and remaining 2 tablespoons of cider. Whisk until smooth. (Caramel sauce can be cooled and refrigerated for several days; warm briefly in the microwave or on the stovetop, until it’s a “drizzle” consistency, before assembling.)
5 Assemble the monkey bread: Grease a bundt pan well and set aside. Melt the butter needed for assembly. In a separate bowl, mix together the sugar and cinnamon.
Tear off walnut- or golf ball-sized pieces of dough and roll into balls between your hands, They don’t have to be uniform! Dip each dough ball into the melted butter, roll in cinnamon sugar, and place in the bottom of the prepared bundt until there is a good layer on the bottom of the pan (using up about half the dough).
Spoon all of the apples over the dough, followed by a third of the caramel sauce. Continue rolling the remaining dough and layering in the pan. Drizzle another third of the caramel sauce over the top. (Save the rest of the caramel sauce for serving).
6 Let the monkey bread rise for 30 to 60 minutes: Cover the monkey bread with plastic wrap. Room temperature dough will take about 30 minutes to rise; dough that’s cold from the fridge will take 30 to 60 minutes. Let the monkey bread rise until the top looks slightly puffed and pillowy.
7 Preheat the oven to 350°F.
8 Bake the monkey bread: Uncover the bundt pan and transfer to a sheet pan (to catch butter drips!). Place in the oven and bake for 30 to 35 minutes. When done, the top should have risen slightly over the top of the pan and the bread should be a deep golden brown.
9 Cool and serve! Cool the monkey bread in the bundt pan on a wire rack for 15 minutes. Place a serving plate over the pan, and using oven mitts, flip the pan over to unmold the monkey bread onto the plate.
Drizzle with the remaining caramel sauce and serve. Be careful, the bread will still be hot!