Prep the basics: Heat the oven to 350°F (175°C). Line two baking sheets with parchment. Soften butter and cream cheese.

Mix dry ingredients: In a bowl, whisk 1 1/4 cups flour, 1 1/2 cups rolled oats, 1/2 teaspoon baking soda, 1/2 teaspoon baking powder, 1/2 teaspoon salt, 1 teaspoon cinnamon, 1/2 teaspoon ginger, 1/4 teaspoon nutmeg, and a pinch of cloves.

Cream the butter and sugars: In a large bowl, beat 1/2 cup unsalted butter with 1/2 cup brown sugar and 1/4 cup granulated sugar until light and fluffy, about 2 minutes.

Add wet ingredients: Beat in 1 egg yolk, 1/2 cup pumpkin puree, and 1 teaspoon vanilla. Scrape the bowl. The mixture may look slightly curdled—this is fine.

Combine: Add dry ingredients and mix on low until just combined. Do not overmix. The dough should be thick and slightly sticky.

Scoop and bake: Scoop 1 1/2-tablespoon mounds onto sheets, 2 inches apart. Gently flatten each mound to about 1/2 inch thick for even baking. Bake 10–12 minutes, until edges are set and centers look soft.

Cool completely: Let cookies rest on the sheet for 5 minutes, then transfer to a rack. Cool fully before filling.

Make the filling: Beat 4 ounces cream cheese with 4 tablespoons unsalted butter until smooth. Add 1 1/2 cups powdered sugar, 1 teaspoon vanilla, a pinch of salt, and 1–2 teaspoons milk or cream. Beat until fluffy and spreadable.

Assemble: Pair similar-sized cookies. Pipe or spread 1–2 tablespoons filling on the flat side of one cookie. Top with its match and press gently until the filling reaches the edges.

Set and serve: Chill assembled pies for 20–30 minutes for cleaner edges, or serve right away for extra softness.