Preheat the oven to 350° F. Line a large baking sheet with parchment paper.
In the bowl of a stand mixer, beat together the sugar, brown sugar and butter for about 3 minutes.
Beat in the eggs, one at a time until thoroughly mixed in. Add in the vanilla extract and combine. Add in the pumpkin and thoroughly combine with the other wet ingredients.
In a separate, large bowl whisk together the flour, baking soda, 3 teaspoons of cinnamon, ginger, allspice, nutmeg, salt and baking powder.
Add the dry ingredients to the wet mixture in two or three additions until everything is just combined.
Drop the dough onto the prepared baking sheet using a 1½ tablespoon scoop, spacing them about 2 inches apart.
Bake the cookies for 18 minutes until they are baked all the way through. Remove the cookies to a cooling rack to cool thoroughly.
Make the icing:
In a small bowl whisk together the confectioner's sugar and ½ teaspoon of cinnamon. Stir in the milk until it creates a thick icing.
Spoon the icing over the top of each cookie, then place them on a cooling rack to let the icing set: about 1 hour.
Serve them up, or store the cookies in a sealed contained for up to three days.
Makes about 48 cookies.
What can I do with leftover pumpkin puree?Store any leftover pumpkin puree in a sealed container in the fridge for up to one week. Or, scoop it into a freezer-safe resealable bag and freeze the puree for up to 3 months. Use extra puree in quick bread, soups, smoothies—there are so many possibilities. Here's a collection of pumpkin puree recipes for inspiration.Can these cookies be frozen?Yes! Once the icing has set, freeze the cookies in a single layer in a freezer-proof bag or dish for up to two months. Allow the sealed cookies to thaw in the refrigerator. The day you want to serve them, let them sit out at room temperature with the cover or bag opened a crack, so that no condensation collects on the icing, until they're no longer cold. (Or, freeze them un-iced.)You can also freeze the cookie dough to bake up later. Store the dough tightly wrapped for up to three months. Allow the dough to thaw in the fridge before scooping and baking. Check the cookies for doneness after 15 minutes.
Check the label carefully when buying pumpkin at the store. What you want for these cookies is pure pumpkin puree. It's easy to get it confused with pumpkin pie mix, also sold in cans.
Use softened butter so that it will properly aerate when blended with the sugars. Leave it out at room temperature to soften, or try one of these tricks to soften butter faster.
A cookie scoop is great for this recipe: it makes it easy to portion the sticky dough onto the baking sheet. Here are the cookie scoops I use. (affiliate link.)
Bake the cookies until they're just set and light—don't overbake or they'll be dry.
The cinnamon icing should be thick enough to cover the top of the cookie without soaking in. If your icing seems thin, whisk in more confectioner's sugar to thicken it.
Once the cookies are iced, let them set at room temperature until the icing is firm. If you need to stack the cookies, place pieces of wax paper between layers so they don't stick.