How to Make Chocolate Babka:

Cup of Yum
1. In the bowl of a stand mixer with the whisk attachment, add warm milk, sprinkle top evenly with yeast and let sit for 7 min. Whisk in ½ cup flour and 2 Tbsp sugar. Cover with plastic wrap and let rise in a warm oven (100˚F) for 25-30 min or at room temp 35-45 min until puffed.
2. Whisk in eggs, 3 Tbsp melted butter, remaining 2 Tbsp sugar, salt, and vanilla. Using the dough hook on speed 2, add the remaining 3 cups of flour (1/2 cup at a time, letting it incorporate between additions). The dough should feel barely sticky to the touch but should not stick to the sides of the mixing bowl. Add an extra 1-2 Tbsp flour if needed. Once all flour is in, continue kneading on speed 2 for 8-10 min.
3. Cover with plastic wrap and let rise in a warm oven for 1 hr or at room temp 2 hrs, until doubled in size. Meanwhile, make the chocolate ganache (instructions below).
4. Once the dough has risen, divide it in half. Generously dust flour on a clean work surface and place 1 piece of dough in the center. Sprinkle dough with flour and roll into a 12" wide by 16" long rectangle. Spread with 1/3 of the ganache. Roll the dough up tightly starting with the shorter side.
5. Cover with plastic wrap and refrigerate for 15 min. Cut each chilled roll in half lengthwise with a sharp knife, keeping the top 1/2" of the roll connected. Twist halves together a few times.
6. Butter and line 2 loaf pans with parchment paper. Carefully transfer the dough to the prepared pans. Cover with plastic wrap and let rise in a warm place for 30-45 min or at room temp for 1 to 1½ hours or until puffy. Preheat oven to 350˚F.
7. Brush loaves with remaining 1 Tbsp melted butter and Bake at 350˚F on the center rack for 30 min or until golden brown. Brush hot loaves with coconut oil to give them a sheen or spread the remaining chocolate ganache over the tops.

How to Make Chocolate Ganache:

1. In a small saucepan over medium heat, combine heavy whipping cream with 1/4 cup sugar, stirring until dissolved and cream reaches a simmer then remove from heat.
2. Add chocolate chips to a medium bowl and pour the hot cream over the top, wiggling the bowl around to ensure the chocolate chips are covered. Cover the bowl and let sit for 5 minutes. Uncover and whisk starting from the center and moving outward until a smooth chocolate sauce has formed. Cool completely to room temperature or until the sauce has thickened. To speed set, refrigerate the ganache for 10 minutes at a time, whisking to check the consistency.