Prep your tools. Line two baking sheets with parchment. Have plastic wrap ready for chilling the dough. Preheat the oven to 350°F (175°C) once your dough is chilling.

Mix the dry ingredients. In a medium bowl, whisk 2 1/2 cups all-purpose flour, 1 teaspoon baking powder, 1/2 teaspoon salt, 1 teaspoon cinnamon, 1/4 teaspoon nutmeg, and a pinch of cloves. Set aside.

Cream the butter and sugar. In a large bowl, beat 3/4 cup softened unsalted butter with 3/4 cup granulated sugar until light and fluffy, about 2 minutes. This creates a tender texture.

Add pumpkin and flavor. Beat in 1/2 cup pumpkin purée (well-blotted with paper towels to remove excess moisture), 1 egg yolk, and 1 teaspoon vanilla. Mix until smooth. The mixture may look slightly curdled at first; that’s fine.

Combine wet and dry. Add the dry ingredients to the wet in two additions. Mix on low until no dry streaks remain. The dough should be soft but not sticky; if it’s very sticky, sprinkle in 1–2 tablespoons more flour.

Roll out the dough. Divide dough in half. On a lightly floured sheet of parchment, roll each half into a 9x12-inch rectangle about 1/4 inch thick. Keep edges as straight as you can for tidy swirls.

Make the filling. In a small bowl, mix 1/2 cup brown sugar, 2 teaspoons cinnamon, and a pinch of salt. Brush the dough with 3 tablespoons melted unsalted butter, then sprinkle the cinnamon sugar evenly over the surface, leaving a 1/2-inch border on one long edge.

Roll into a log. Starting from the long edge opposite the border, roll the dough into a tight log. Use the parchment to help lift and roll evenly. Seal the seam by pinching gently and roll the log seam-side down.

Chill for clean slices. Wrap each log in plastic and chill for 45–60 minutes, or freeze for 20–25 minutes, until firm but sliceable. Don’t skip this—it keeps the spirals intact.

Slice and bake. Using a sharp knife or unflavored dental floss, slice 1/2-inch rounds. Place 2 inches apart on prepared sheets. Bake at 350°F (175°C) for 11–13 minutes, until edges look set and the bottoms are just turning golden. They should still be soft in the center.

Cool before glazing. Let cookies rest on the sheet for 5 minutes, then transfer to a rack to cool.

Glaze. For a simple vanilla glaze, whisk 1 cup powdered sugar with 1–2 tablespoons milk and 1/2 teaspoon vanilla until smooth and drizzleable. For a cream cheese glaze, beat 2 ounces softened cream cheese with 1 tablespoon butter, 1 cup powdered sugar, 1 teaspoon vanilla, and enough milk to thin. Drizzle over cooled cookies so it sets nicely.