Sweet Braided Easter Bread

Combine milk, oil, salt, orange extract, 2 room temperature eggs, sugar, orange zest, 4 cups flour, and yeast in a bread machine, in that order. Set to Dough cycle and start the machine; be sure to peek inside while dough is mixing and add additional flour as needed to create a soft, but not wet, dough.

Transfer dough to an oiled bowl and let rise until doubled in size, about 1 hour.

Meanwhile, bring a medium pot of water to a boil over medium-high heat. Reduce heat to a rapid simmer, add 4 whole eggs, and simmer for 6 minutes. Remove from heat and transfer eggs to a bowl of ice water to cool quickly.

Punch risen dough down and turn onto a floured surface. Divide into 3 equal pieces. Roll each piece to form a 12-inch-long rope, about 1 1/2 inches thick. Braid pieces together, pinching the ends. Loop into a circle, pinch the ends to close, and place on a parchment paper-lined baking sheet. Remove eggs from the bowl of ice water, dry, and arrange evenly atop the braid. Push in gently, about 1/3 of the way down. Cover and let rise again, about 1 hour.

Preheat the oven to 350 degrees F (175 degrees C).

Whisk together remaining room temperature egg, 2 tablespoons water, and anise extract in a small bowl until well combined. Brush braid with egg wash, avoiding boiled eggs; otherwise, while baking, they will have cooked wash on them and won't dye nicely.

Bake in the preheated oven, switching between another parchment-lined baking sheet every 10 minutes throughout baking time to prevent the bottom from getting too dark, until browned, about 30 minutes. Remove from the oven and let cool thoroughly, 20 to 30 minutes.

Paint eggs on bread with liquid food dye. Be careful not to drip dye onto bread. Let dry for about 10 minutes. Brush bread with anisette liqueur and let dry before serving, about 5 minutes more.