In a large mixing bowl, combine the all-purpose flour, sugar, salt, and active dry yeast. Cut in the cold butter until the mixture resembles coarse crumbs. Gradually add in the milk and egg, mixing until a soft dough forms. This process should take about 5 minutes.

Cover the dough with plastic wrap and refrigerate for at least 30 minutes. Chilling allows the butter to firm up, ensuring that the Wisconsin Apple Kringle has a flaky texture once baked.

Preheat your oven to 375°F (190°C). On a lightly floured surface, roll out the chilled dough into a large oval shape, about 1/4 inch thick. Spread the spiced apple filling generously down the center of the dough, leaving edges to fold over. Carefully fold the dough over the filling, pinching the edges to seal, and form into an oval or horseshoe shape on a lined baking sheet.

Place the shaped kringle in the preheated oven and bake for 25–30 minutes, or until it is golden brown and the filling is bubbling slightly. Keep an eye on the kringle in the last few minutes for a perfect golden hue.

Once baked, allow the Wisconsin Apple Kringle to cool for about 10 minutes on a wire rack. In a small bowl, whisk together the powdered sugar and vanilla extract until smooth. Drizzle this sweet glaze over the warm kringle.