For the Brioche dough

In a bowl, combine the yeast and warmed milk (110F) and let stand until foamy, about 5 minutes

In the bowl of stand mixer fitted with the dough hook, add the yeast mixture,  flour, salt, and sugar, and mix to combine.

Add the eggs and egg yolk, and continue mixing on low for 5 minutes or until the dough no longer sticks to the sides of the bowl.

Add the softened butter and mix for another 15 min, until the dough no longer sticks to the sides of the bowl.

Lightly oil a separate glass bowl. Form the brioche dough into a bowl and transfer to oiled bowl. Cover with plastic wrap and refrigerate overnight. Dough should double in size.

Remove the dough from the fridge and place on a lightly floured surface. Divide in half (I didn't weigh it, but you can if you want to get exact loafs).

Lightly flour your rolling pin and roll out one half of the dough to 11"x15", approximately.

Using an offset spatula, spread half the chocolate filling, careful to not spread all the way to the edges. Leave about 1/2 inch border. Starting at the long edge nearest you, tightly roll up the dough rectangle into a tight log. Repeat with the other dough half.

For a traditional babka loaf, using a sharp knife cut through the middle length-wise. Place one piece of the though over the other, and braid together. Place the babka in a 9x4 or 10x5 inch pan (greased and lined), cover and allow to rest for 2 hours. Repeat with the second half of the dough.

For a brioche loaf, cut the log in half crosswise. Place one half over the other, forming a cross. Twist to form a spiral and transfer to a grease and lined loaf pan. Cover and allow to rest for 2 hours.

Preheat the oven to 350F, and brush edges of dough with egg wash.

Bake for 30-35 minutes, until puffed and golden brown. Allow to cool slightly before removing from pan.

Serve warm with spreadable butter, optional but delicious.

For the Chocolate Orange filling

In a medium saucepan, combine the butter, sugar, cocoa powder, espresso, cinnamon and salt. Once butter has melted and all the ingredients are combined, remove from heat. Add the orange extract and chopped chocolate. Stir until chocolate melts and the mixture is fully incorporated.

Allow to cool for 15-10 min.