Ingredients
Equipment
Method
Make cinnamon crumble
- Combine flour, brown sugar, and cinnamon, then cut in cold butter until the mixture looks like coarse crumbs with no dry flour left.
- Refrigerate the crumble while you prepare the cookie dough.
Mix pumpkin cookie dough
- Preheat the oven to 375°F and line a sheet pan for baking.
- Beat softened butter and brown sugar until smooth, then add blotted dry pumpkin, egg yolk, and vanilla and mix until combined.
- Fold the flour mixture into the pumpkin mixture just until no dry streaks remain.
Assemble and bake
- Scoop 2-tablespoon rounds of dough and place them on the sheet pan with space between cookies.
- Press a generous pinch of chilled cinnamon crumble into the top of each cookie so it adheres.
- Bake for 12-14 minutes at 375°F until the edges look set and the tops are lightly golden.
Glaze and finish
- Cool cookies until no longer hot to the touch so the glaze doesn’t melt away.
- Whisk powdered sugar, cream cheese, milk, and cinnamon until smooth, then drizzle over the cooled cookies.
Notes
For best crumble texture, keep it cold—refrigerating 15 minutes helps it stay buttery and forms a sweet top while baking. Store cookies in an airtight container at room temperature for up to 3 days or refrigerate for up to 5 days; freeze baked cookies (without glaze) for up to 2 months and glaze after thawing. For a gluten-free swap, use a 1:1 gluten-free baking flour blend in place of all-purpose flour.