Warm the milk in a saucepan over medium-high heat until it steams but does not boil, then remove from heat and allow it to cool to 110–115°F (approximately 10–15 minutes). Meanwhile, sprinkle the yeast over the lukewarm water in a small bowl and let it sit until it becomes foamy, roughly 5 minutes. Melt the butter and let it cool briefly. In a large bowl, whisk the eggs, sugar, salt, and the cooled melted butter together. Add the cooled milk and the yeast mixture, stirring to combine. Begin adding the flour gradually—start with about 6 cups in portions, then add the remaining flour one cup at a time until you have incorporated all 8 1/2 cups and the dough is sticky but cohesive. Avoid overmixing to keep the dough tender.

Lightly oil a very large bowl and transfer the dough into it, turning the dough so all surfaces are coated with oil. Cover the bowl with plastic wrap and a tea towel, then set it in a draft-free location to rise until doubled in volume, about 1–2 hours. Punch the dough down to deflate it, cover again, and refrigerate for at least 4 hours or overnight for optimal flavor and texture. Line two baking sheets with parchment paper. With lightly oiled fingertips, portion the dough and shape it into balls about 2 1/2 inches in diameter, arranging them on the prepared sheets.

In the bowl of a stand mixer, combine the softened cream cheese and pumpkin puree. Beat on high speed for 3–4 minutes until smooth, scraping down the sides of the bowl every minute. Add the brown sugar, vanilla extract, nutmeg, ginger, cloves, and salt, then beat for an additional 2–3 minutes until the filling is fluffy. Transfer the filling to the refrigerator until you are ready to use it.

Press an indentation into the center of each dough ball using your fingers and thumbs. Spoon about 1 teaspoon of the chilled pumpkin filling into each indentation. Cover the filled rolls with a clean sheet of parchment and a tea towel, then let them rise in a warm spot until nearly doubled, approximately 1 hour.

In a bowl or food processor, combine the flour, sugar, cold butter pieces, and cinnamon. Mix with your fingertips or pulse until the mixture forms fine crumbs to create the streusel topping.

Preheat the oven to 375°F and arrange the racks in the center and lower positions. Sprinkle the streusel topping evenly over the risen, filled kolaches. Bake for 25–30 minutes, rotating the sheets every 10 minutes, until the kolaches are golden brown. Allow them to cool for 20 minutes before serving. To reheat leftovers, bake at 350°F for approximately 10 minutes.