Prep time1 hour, plus overnight rest
Cook Time1 hour
Yield1 large braided bread
For the dough
400 grams (3 1/3⅓ cups) all-purpose flour
240 mL (1 cup) whole milk
112 grams (½ cup, 1 stick) unsalted butter, room temperature
1 egg (65 grams)
50 grams (¼ cup) granulated sugar
7 grams (2 ¼ teaspoons, 1 packet) instant yeast
8 grams (1 ½ teaspoons) kosher salt
½ teaspoon (2.5 mL) coconut extract, optional but recommended
For the filling
450 grams (1 pound, about 2 ¾ cups) cubed fresh pineapple
100-150 grams (½ to ¾ cup) granulated sugar (see note)
50 grams (½ cup) unsweetened shredded coconut, toasted if desired
14 grams (1 tablespoon) unsalted butter
15 grams (2 tablespoons) cornstarch
For the glaze
100 grams (1 cup) powdered sugar, sifted
½ teaspoon coconut extract (optional, recommended)
1-2 tablespoons hot water (enough to make a drippy glaze)
In the bowl of a stand mixer fitted with the dough hook or a large mixing bowl, combine all the ingredients for the dough and mix on low speed or knead until a smooth dough forms—up to 15-20 minutes. It will be very soft and fairly sticky, but when done it should mostly stick to itself rather than to the bowl or your hands.
Transfer the dough to a lightly greased bowl, cover tightly, and immediately place it in the refrigerator to chill for at least 12 (and up to 15) hours. The dough will rise slowly overnight and will firm up substantially.
While the dough is rising, make the filling. Combine the pineapple and the sugar (see note) in a Milo Mini Dutch, place over medium heat, and cover. Allow the fruit to cook for 5-8 minutes, stirring occasionally. It will get very juicy and soft.
Gently mash the pineapple with a wooden spoon to make a texture similar to preserves. Stir together the coconut and cornstarch so that cornstarch no longer has clumps. Stir the coconut, cornstarch, and butter into the pineapple mixture and allow to come to a boil for 1 full minute.
Remove the filling from the heat and cool completely (chilling overnight is preferable) before using.
The next day, remove the dough from the fridge and turn it onto a lightly floured surface. Roll the dough into a rectangle about 10 x 15 inches.
Use a knife or a bench scraper to cut strips approximately 1 inch wide by 3 inches long along each side of the dough, leaving the strips attached to the center and not cutting all the way across. You want to leave a “path” at least 3 inches wide in the center of the dough for the filling. See the illustration below for further explanation.
Spoon the filling evenly over the uncut path of dough in the middle. Lift a strip from one side of the dough and fold it down diagonally over the filling. Repeat with a strip on the other side of the dough, layering the end over the first strip. Repeat this pattern, alternating sides, all the way down the length of the bread.
Gently lift the shaped and filled bread onto a half sheet pan lined with a Precut Parchment Paper Sheet. Tuck the ends of the bread under themselves to seal the edges. Cover and allow to rise for 1-2 hours, until noticeably puffy and risen. In the meantime, preheat the oven to 350°F.
Bake the braided bread for 40-45 minutes, until the internal temperature of the bread (not the filling) is at least 190°F or until it is deep golden brown all over the surface. Remove from the oven and cool completely on the baking pan set on top of a wire rack.
Make the glaze by combining the powdered sugar, coconut extract if using, and one tablespoon of hot water in a small bowl and whisking until smooth. If needed, add additional hot water until the glaze is drippy but not runny. Drizzle the glaze over the cooled bread and serve immediately.