Preheat the oven to 350°F (convection). Line a baking sheet with parchment paper and set aside.

In a large bowl or stand mixer fitted with the whisk or paddle attachment, beat the room-temperature butter and granulated sugar until light and off-white in color, about 1–2 minutes.

Add the egg and vanilla extract, mixing until fully combined.

Add the all-purpose flour, baking powder, and baking soda. Gently fold the dry ingredients into the dough until no dry spots remain.

Scoop ⅓ cup portions of cookie dough and place onto the prepared baking sheet, spacing evenly apart.

Bake for 11–12 minutes, until the edges are set and the centers look slightly underbaked.

For perfectly round cookies, use a round bowl, cup, or cookie cutter to gently swirl around the cookies immediately after removing them from the oven.

Allow the cookies to rest on the baking sheet for about 10 minutes before transferring.

Strain the canned pumpkin using a cheesecloth or paper towels until very little liquid remains.

In a bowl, mix together the brown sugar, cinnamon, drained pumpkin, and pumpkin pie spice to create the pumpkin brown sugar mixture.

For the frosting, beat the butter until light and off-white. Add the powdered sugar and mix until fully incorporated and slightly thick. Add the heavy cream and extracts, then whip until light and fluffy.

Spread about 1 tablespoon of the pumpkin brown sugar mixture onto each cookie, then pipe or swirl the frosting on top.

Enjoy fresh, or store cookies in an airtight container in the refrigerator for up to 8 days.