First, make sure you have removed excess liquid from the pumpkin puree by blotting it as much as you can with a clean kitchen tea towel or paper towels. This dough will not turn out properly with the pumpkin’s excess moisture. After blotting excess liquid, you should have about 1/3 cup (75g) to use in the recipe. See recipe note.
In a large bowl using a hand mixer or a stand mixer fitted with a paddle attachment, beat the butter and sugar together on high speed until completely smooth and creamy, about 3 minutes. (Here’s a helpful tutorial if you need guidance on how to cream butter and sugar.) Add the pumpkin and vanilla extract, and then beat on high speed until combined, about 1 minute. Scrape down the sides and up the bottom of the bowl and beat again as needed to combine. It’s ok if the mixture looks curdled. Add the flour, pumpkin pie spice, cinnamon, baking powder, and salt. Beat on low speed until combined and a thick dough forms. Divide the dough into 2 equal parts. If you want to be accurate and weigh the dough, each half should be around or a little more than 12 ounces each. On a floured work surface using floured hands, pat each into a small rectangle. Then, using a lightly floured rolling pin, roll each portion of dough out into a 10×8 inch rectangle. It should be about 1/4″ thick. As you’re rolling, use your hands to help keep the sides straight as you see me do in the video. Spread half of the melted butter onto each rectangle doesn’t need to be exactly half, just eyeball it. It will be a thick layer of butter. Mix the brown sugar, pumpkin pie spice, and cinnamon together then sprinkle evenly over each. Using the back of a spoon, pat the brown sugar and spices down into the butter to help it stick. Working slowly using your fingertips, tightly roll up each rectangle into a 10-inch log. If the dough is cracking at all, use your fingers to smooth it out. (See troubleshooting above if needed.) Wrap the dough logs in plastic wrap, parchment paper, or aluminum foil. Chill the dough logs for at least 2 hours and up to 3 days in the refrigerator. (Or freeze for up to 3 months, see freezing instructions below.) The pictured cookie dough logs chilled in the refrigerator for 1 day.
Preheat oven to 350°F (177°C). Line large baking sheets with parchment paper or silicone baking mats.
Remove dough logs from the refrigerator. Using a sharp knife, cut each into slices that are slightly less than 1/2 inch (between 1/4 and 1/2 inch is perfect). You’ll have around 24-26 cookies per log. Arrange sliced cookies onto baking sheets 1.5-2 inches apart. If the slices have lost their round shape, use your fingers to help mold them into perfect circles again. Not necessary of course, but you can see me do it in the video. Bake for 13-15 minutes or until very lightly browned around the bottoms. (As the cookies bake, you can make the icing in the next step.) Remove finished cookies from the oven, allow to cool on the baking sheet for 10 full minutes, and then transfer to a wire rack.
In a large bowl using a handheld or stand mixer fitted with a paddle or whisk attachment, beat the cream cheese on high speed until completely smooth and creamy, about 1 minute. Add the butter and beat until smooth and combined. Add the confectioners’ sugar and vanilla extract, and then beat on medium speed until combined. Taste. Add a pinch of salt if desired. Spread cream cheese frosting (or drizzle maple icing) on warm or cooled cookies.
Cover plain or iced cookies and store at room temperature for up to 2 days or in the refrigerator for up to 1 week.
