In a KitchenAid bowl, add milk, yeast, and some of the sugar. Let sit for several minutes until yeast is activated.
Whisk in 1/4 cup flour and some more sugar. Cover with plastic wrap and let sit in a slightly preheated oven (~100F) until puffy.
Remove from oven, add remainder of sugar, egg, butter, salt, vanilla, and buttery extract. Mix to combine.
Using the dough hook, start adding flour and knead until the dough doesn’t stick to the sides of the mixing bowl.
Cover with plastic and let rise until double in size.
Once risen, roll into a rectangle. Spread with the ganache, and roll tightly (starting with the shorter side).
Make a braid and let sit in a lightly preheated oven (~100F) until double in size.
Sprinkle pearl sugar, and egg wash. Bake for ~25min.
Brush hot loaf with sugar syrup and the rest of the ganache.