Rich & Fluffy Chocolate Sweet Rolls

These rich and fluffy chocolate sweet rolls come together with a buttery soft fresh homemade dough and brown sugar chocolate filling. Theyre shaped like cinnamon rolls but taste like flaky chocolate babka. You can make the chocolate rolls within a few hours or get started the night before using the overnight preparation option.
Ingredients
1 cup 240ml whole milk warmed to about 100F 38C
6 Tablespoons 75g granulated sugar divided
1 Tablespoon 9g active dry or instant yeast
5 Tablespoons 71g unsalted butter melted and slightly cooled

2 large eggs at room temperature
1 teaspoon salt
4 cups 530g bread flour spooned leveled plus more as needed for handswork surface
Chocolate Filling
6 Tablespoons 85g unsalted butter softened to room temperature
12 cup 100g packed light or dark brown sugar
2 Tablespoons 10g unsweetened natural or dutch process cocoa powder
1 teaspoon ground cinnamon
1 teaspoon pure vanilla extract
34 cup 135g semisweet chocolate chips or a 4 ounce semisweet chocolate bar finely chopped
Espresso Icing
3 Tablespoons 45ml heavy cream
1 teaspoon espresso powder
1 and 12 cups 180g confectioners sugar sifted sift after measuring
12 teaspoon pure vanilla extract
Instructions
Prepare the dough Whisk the warm milk 2 Tablespoons sugar and the yeast together in the bowl of your stand mixer fitted with a dough hook or paddle attachment. Cover and allow mixture to sit for about 5 minutes or until foamy on top. If you do not own a mixer you can do this in a large mixing bowl and in the next step mix the dough together with a large wooden spoonsilicone spatula. It will take a bit of arm muscle. A hand mixer works but the sticky dough repeatedly gets stuck in the beaters. Mixing by hand with a wooden spoon or silicone spatula is a better choice.
Add the remaining sugar the butter eggs salt and 1 cup about 130g of flour and beat on medium speed for 1 minute. Scrape down the sides of the bowl with a rubber spatula. Add 3 cups about 400g flour switch the mixer down to low speed and beat until a soft dough forms and pulls away from the sides of the bowl. Dough will be very soft but not overly sticky. Beat in 23 more Tablespoons of flour if dough seems very sticky. Avoid adding more flour than you need
Knead the dough Keep the dough in the mixer and switch to the dough hook if using the paddle and beat for an additional 68 full minutes or knead by hand on a lightly floured surface for 68