DOUGH:
1 - In the bowl of a stand mixer fitted with a whisk attachment, combine warm milk, 2 Tbsp of sugar and yeast. Lightly whisk together. Let proof for 5 minutes, until frothy. Add in the remaining sugar and eggs, mix to combine. Add vanilla, mix to incorporate. Swap the mixer attachment to a dough hook. Add the flour, then place the salt on top of the flour. Knead until the dough starts to come together. Add in butter, knead for an additional 5 minutes, until a soft dough forms.
2 - Transfer the kneaded dough into a large, greased bowl. Cover with plastic wrap and place into the fridge overnight. Remove from the fridge and place onto the counter to let the dough finish rising and come to room temperature.
FILLING:
1 - In a microwave safe bowl add chocolate chips and butter and microwave for 1 minute, mix until smooth. Add in the powdered sugar, cocoa, vanilla and salt and whisk together until smooth. Set aside.
SIMPLE SYRUP:
1 - In a small saucepan combine water and sugar. Bring to a simmer over medium-low heat. Once simmering, constantly whisk until the sugar has dissolved. Continue simmering for 5 minutes, until the mixture has slightly thickened.
Assembly:
1 - Once the dough has risen, roll out onto a clean, lightly floured surface into a 14”x16” rectangle. Spread the chocolate mixture evenly over the dough. Roll the dough up, then turn it so one end of the dough log is facing you. Use a sharp knife to make a cut down the center of the dough log, lengthwise. Lay each dough piece face up, right next to each other. Pinch the top 2 ends together. Pull the right side over the left, then the left over the right. Repeat 3 times, then twist the ends together. (see photos in post)
2 - Transfer the loaf to a well greased loaf tin. At this point, you can either cover the loaf and place it into the fridge to rise overnight, or leave it out on the counter to rise at room temperature for about 30 minutes. If you choose to use the fridge method, after rising overnight let the loaf sit out on the counter for about 30 minutes to allow it to come to room temperature.
3 - Towards the end of the rise time, preheat the oven to 350°F. Once risen, place the loaf into the preheated oven on the center rack. Bake for 30 minutes. Once it has baked for 30 minutes, tent the loaf with a piece of tin foil. Continue baking for an additional 40 minutes. Once baked, remove from the oven and place onto a wire cooling rack. While the bread is hot, brush with the simple syrup mixture.