1-First, in the bowl of an electric stand mixer fitted with a dough hook, combine 2 ½ cups bread flour, ¼ cup granulated sugar, 1 teaspoon salt, and 2 ¼ teaspoons instant yeast. Add 1 cup warmed whole milk and ¼ cup melted unsalted butter, then mix on low speed until the dough begins to form.

2-Mixing and Rising the Dough: Gradually incorporate the remaining flour, increase to medium speed, and mix for about 1 minute until a soft dough forms. Continue beating on medium-high speed for 6 minutes until the dough pulls away from the bowl sides and is no longer sticky. Add 1 ⅓ cup roughly chopped dried cherries on low speed until fully incorporated, then shape the dough into a ball, place it in a greased bowl, cover, and let it rise in a warm place for 1 hour or until doubled in size.

3-Next, for the filling, melt 2 ounces coarsely chopped bittersweet chocolate and 2 tablespoons unsalted butter over simmering water, stirring continuously until smooth. Remove from heat, stir in 2 tablespoons confectioners’ sugar and ½ tablespoon unsweetened cocoa powder, then set aside to cool until spreadable but not runny.

4-Shaping and Baking: Grease a 9×5 inch loaf pan, punch down the risen dough gently, and roll it out into an 8×13 inch rectangle on a floured surface. Spread the chocolate filling evenly over the dough, leaving a ½ inch border uncovered, then roll the dough tightly from the longer side and place seam side down. Cut the log in half lengthwise, with the cut sides facing up, braid the two halves together, and pinch the ends to seal. Transfer the braid to the prepared loaf pan, tucking the ends under, then cover and let it rise for 1 hour or until doubled.

5-Preheat the oven to 350°F and bake the bread for 25-30 minutes until golden brown. Allow it to cool in the pan on a wire rack for 10 minutes, then transfer to the rack to cool completely.