Prepare a large sheet pan by lining with parchment paper or a silicon baking mat to avoid burned cookie bottoms. Preheat oven to 350℉.
Add flour, baking soda, baking powder, cinnamon, pumpkin pie spice, and salt to a large bowl; whisk to combine and set aside.
In a medium bowl, cream together butter, granulated sugar, and brown sugar until smooth and creamy. Add 1 cup pumpkin, egg, and vanilla. Beat until mixture is creamy. Add in dry ingredients and mix until just combined. Avoid overmixing, as it will create dense cookies.
Optionally, cover tightly and chill dough for 30 minutes up to 10 hours. Chilling is not necessary, but it makes dough much easier to work with and intensifies flavors.
Use a 1 tablespoon measuring spoon to scoop out balls of dough onto the lined sheet pan. Try to smooth or round the balls, but it’s okay if they’re a bit bumpy. (Chill in the fridge for additional time if needed to make it easier to get cookie dough balls on a tray). Leave 2 inches between each cookie (I only bake 8–10 cookies at a time) and flatten balls of dough slightly.
Bake for 8–13 minutes (9–10 minutes is perfect for my oven), watching carefully to avoid over-baking. I like these slightly under-baked and soft, but the tops shouldn’t be shiny or wet looking at all. Remove and allow cookies to stand for 3–5 minutes on the sheet pan before moving to a wire cooling rack.
Meanwhile, make frosting. In a stand mixer fitted with the whisk attachment (or a large bowl and a hand mixer), beat softened (not melted) cream cheese and butter until creamy for about 2 minutes at medium-high speed. Add powdered sugar, salt, and vanilla. Beat until combined and frosting is soft and creamy. Avoid over-beating the mixture or you’ll get whipped frosting.
Generously frost half the cooled cookies. Sandwich the other half of the cookies on top.
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Notes
Note 1: If you press a measuring cup into a bag of flour, you will pack in way too much flour; use a spoon to scoop it into a measuring cup, then level the top with the back of a table knife.Storage: Do not store the cookies in plastic containers. Store on plates loosely covered with foil in the fridge. Best eaten same day or within 1–2 days. After that, they soften too much and the texture degrades. Freeze unbaked cookie dough balls for up to 3 months; bake straight from freezer for an additional 1–3 minutes.