I recently tried this recipe because Kari found it online and wanted to taste it. It’s a bit fussy, and I ended up with not enough cookie dough and too much streusel topping, but it makes a sweet, chewy cookie. There is not a lot of pumpkin compared to the other ingredients — so much of the flavor comes from the streusel and pumpkin spice. These are large cookies, though you should be able to get 16 from the dough and have a little leftover streusel for a small coffee cake.

I did swap in some ginger and rum extracts in place of some of the vanilla, which helps to punch things up a bit. If you have access to something like these (and I absolutely love Auntie Arwen’s for them), it’s a great way to give your baked goods some special notes beyond vanilla (not that there’s anything wrong with vanilla, but come on).

As with any cookie, bring your butter up to room temperature before you get started! Eggs too, if you remember to plan ahead.

Streusel:
6 tbsp unsalted butter, room temperature
3/4 cup brown sugar, packed
3/4 cup flour
2 1/2 tsp pumpkin pie spice (or 1 tsp each of cinnamon and ginger, 1/2 tsp nutmeg)
pinch of salt

Cookie Dough:
1/2 cup pumpkin puree
1 3/4 cups flour
1 tbsp pumpkin pie spice (or 1 tsp each of cinnamon and ginger, 1/2 tsp each of cloves and nutmeg)
1/2 tsp baking powder
1/2 tsp baking soda
1/2 tsp salt
3/4 cup unsalted butter, room temperature
1 cup brown sugar, packed
2 egg yolks, at room temperature
2 tsp vanilla extract (or rum/bourbon/ginger or whatever else sounds good)

Drizzle Icing:
1 cup powdered sugar
1 tsp vanilla extract (or swap in something else for another flavor punch)
2-4 tsp milk

Instructions

Start with the streusel:
Add the butter and brown sugar to a mixing bowl and beat until combined.

Add in the flour, pumpkin pie spice, and salt and beat until the mixture resembles large crumbs.

Chill the streusel in the fridge while making the cookie dough.

Cookie Dough:
Spread the pumpkin puree on a plate and lightly press with a paper towel to absorb the excess liquid. Repeat the step at least four more times, until it’s dry enough that it goes from being ½ cup down to just about a ¼ cup. Hardly any liquid should transfer onto a paper towel once it has been dried enough. Set aside.

Preheat the oven to 350°F. Line two baking sheets with parchment paper.

Whisk together the flour, pumpkin pie spice, baking soda, baking powder, and salt. Set aside.

In a mixing bowl, cream the butter and brown sugar together on high speed for 1-2 minutes until light and fluffy.

Add in the egg yolks and vanilla (or other extracts) and mix on medium speed until pale and fluffy, about 1-2 minutes.

Add the pumpkin and mix on medium-low speed to combine.

Add the dry ingredients and mix just until combined.

Scoop the dough with a 2-tablespoon cookie scoop and drop into balls on the cookie sheet, spacing them out to six per sheet. Make a slight indent in the cookie dough balls using a finger.

Measure out a slightly packed, heaping tbsp of streusel topping and flip it on top of each portion of cookie dough. Press down gently with the palm of your hand to better secure the streusel to the cookie dough. (I found that this placed all of the streusel in the middle with a surprising areola effect, so you might try flattening the dough balls completely and spreading the streusel more evenly across the top.)

Bake the cookies for 11-12 minutes. When the cookies are straight out of the oven, you can use a spatula around the edges to make them more circular if they spread oddly. If you have leftover streusel, you can also add them around the sides where you don’t have much coverage. The butter in the streusel will help this melt on properly if you act quickly enough.

Let them cool for 10 minutes on the cookie sheet, then transfer to a wire rack to cool completely. 

While the cookies cool, make the drizzle icing by mixing the powdered sugar, extract, and milk together in a small bowl until you achieve a drizzle-able consistency. (Start with 2 tsp of milk and add more as necessary.)

Once the cookies are cool, drizzle the icing over them. This will probably look better (i.e., less X-rated) if you use a bag rather than a whisk like I did.