Proof the yeast: In a small bowl, whisk warm milk and a pinch of sugar, then sprinkle yeast over the top. Let sit for 5–10 minutes until foamy.

Make the dough: In a stand mixer bowl, combine melted butter, eggs, remaining sugar, and vanilla. Add the foamy yeast mixture and gradually add flour and salt, mixing until a soft, slightly tacky dough forms.

First rise: Place the dough in a lightly oiled bowl, cover with a kitchen towel, and let it rise in a warm spot for 1 to 1 1/2 hours, until doubled.

Prepare the filling: Mix softened butter, brown sugar, and cinnamon until spreadable. If using, beat in cream cheese.

Shape the cake: Punch down the dough, divide into two equal pieces, and roll each into a long rectangle about 10 by 14 inches. Spread filling evenly and roll each rectangle into a log. Braid the two logs together.

Second rise: Cover loosely and let the braided ring rise for 30–45 minutes until slightly puffy.

Bake: Preheat oven to 350°F (175°C). Brush the ring with melted butter or beaten egg and bake for 20–25 minutes until golden brown.

Let the cake cool for 10–15 minutes. Whisk powdered sugar, milk, and vanilla to a pourable glaze, then drizzle over the warm cake. Sprinkle with colored sugar.

If tradition calls, tuck a small trinket under the cake before serving.