In the bowl of a stand mixer fitted with the dough hook attachment, combine the active sourdough starter, milk, bread flour, eggs, salt, vanilla extract, brown sugar, pumpkin puree, ground cinnamon, and ground ginger.

Mix on low to medium speed until a shaggy dough forms and the ingredients are mostly incorporated. Scrape down the sides and bottom of the bowl as needed.

With the mixer running on low speed, add the softened butter one tablespoon at a time, allowing each addition to incorporate before adding the next.

Once all the butter has been incorporated, increase the mixer speed to medium-high and knead for approximately 7–10 minutes, or until the dough becomes smooth, elastic, and begins pulling away from the sides of the bowl.

The dough will be soft, rich, and slightly sticky because of the butter, eggs, and pumpkin puree. Avoid adding extra flour simply because the dough feels sticky. Adding too much flour can result in dense, dry kolaches rather than a soft, fluffy texture.

Cover the bowl and allow the dough to bulk ferment at room temperature for approximately 6–10 hours, or until it has increased in volume by roughly 30–50%.

It's important to watch the dough, not the clock. Fermentation time will vary depending on the temperature of your kitchen and the strength of your sourdough starter. My kitchen is typically around 67°F (19°C), so my dough tends to ferment more slowly and often takes closer to the longer end of this range. If your kitchen is warmer, the dough will ferment much faster and may be ready sooner. Look for a noticeable increase in volume and a dough that appears slightly puffy and aerated rather than relying strictly on the number of hours.

Optional overnight refrigeration: Once the dough has completed bulk fermentation, cover it tightly and refrigerate overnight. Chilled dough is easier to handle and shape, making this a great option if you want to divide the process over two days.

Line two large baking sheets with parchment paper.

Shape each portion into a smooth ball by gently pulling the edges of the dough toward the center and rolling it against the work surface to create surface tension.

Arrange the dough balls on the prepared baking sheets, leaving several inches between each one.

To check whether the dough is ready, gently press a lightly floured fingertip into the edge of one kolache. If the indentation springs back immediately, the dough needs more time. If it slowly springs back and leaves a slight indentation, the kolaches are ready to fill and bake.

While the dough completes its second rise, prepare the cream cheese filling, pumpkin filling, and brown sugar crumble.

Add the softened cream cheese to a medium mixing bowl and beat until smooth and creamy.

Add the powdered sugar and vanilla extract and mix until completely incorporated and no lumps remain.

Cover and refrigerate until ready to assemble the kolaches.

In a medium bowl, combine the pumpkin puree, brown sugar, all-purpose flour, ground cinnamon, and salt. Stir until smooth and evenly combined.

Cook for approximately 3–5 minutes, stirring frequently, until the mixture thickens slightly and some of the excess moisture has evaporated.

This step is important because pumpkin puree contains a significant amount of moisture. Cooking the filling briefly helps remove some of that water, resulting in a thicker pumpkin topping that stays in place and prevents the kolaches from becoming overly wet or soggy during baking.

Once the mixture is thick enough to hold its shape on a spoon, remove it from the heat and transfer it to a bowl.

Allow the pumpkin filling to cool completely before assembling the kolaches.

In a small bowl, combine the melted salted butter, all-purpose flour, and packed brown sugar.

Stir with a fork until the mixture comes together and forms coarse, buttery crumbs.

Set aside until ready to use. If the crumble is too soft, allow it to cool slightly so the butter can firm up.

Preheat the oven to 350°F (175°C).

In a small bowl, whisk together the egg and milk until smooth to make the egg wash.

Once the kolaches have completed their second rise, gently press into the center of each dough ball using your fingertips or the bottom of a small glass. Create a wide, deep well while leaving a raised border around the outside. Be careful not to flatten the dough completely.

Lightly brush the exposed dough around the edges with the prepared egg wash.

Spoon a generous amount of cream cheese filling into the center of each kolache, dividing it evenly among all 10.

Add a spoonful of the cooled pumpkin filling directly on top of the cream cheese filling. Gently spread it as needed, keeping the filling within the indentation.

Finish each kolache with a generous sprinkling of the brown sugar crumble, dividing it evenly among the kolaches.

Bake the kolaches at 350°F (175°C) for approximately 25–30 minutes, or until the brioche is golden brown and baked through.

If baking both sheets at the same time, rotate the baking sheets halfway through baking to ensure even browning.

Keep an eye on the kolaches toward the end of baking, as the exact time may vary depending on your oven and the size of the kolaches.

Remove from the oven and allow them to cool on the baking sheets for 5–10 minutes before transferring to a wire rack.

In a small bowl, whisk together the powdered sugar, vanilla extract, and 1 tablespoon of milk.

Add additional milk a little at a time until the icing reaches your desired consistency. It should be thick enough to create a beautiful drizzle but thin enough to flow easily from a spoon.

Once the kolaches have cooled slightly, drizzle the vanilla icing generously over the pumpkin filling and brown sugar crumble.

Allow the icing to set slightly before serving.