Preheat oven to 350°F (convection) and line baking trays with parchment paper.

In a stand mixer fitted with the paddle attachment, beat butter and granulated sugar on medium speed until light and fluffy, about 1–2 minutes.

Mix in the egg and vanilla extract until smooth.

In a separate bowl, whisk together flour, baking soda, baking powder, and cinnamon.

Gradually fold the dry ingredients into the wet mixture until a dough forms.

Using about a ⅓-cup scoop, portion cookie dough onto the prepared baking tray, leaving space between each cookie.

Bake for 12–13 minutes, until the edges are lightly golden.

For perfectly round cookies, swirl a cookie cutter or glass around each cookie right out of the oven.

Let cookies rest on the tray for 10 minutes before transferring to a cooling rack.

In a stand mixer, beat butter until creamy and pale. Gradually add powdered sugar until incorporated.

Mix in drained pumpkin (use a cheesecloth), pumpkin pie spice, salt, cinnamon, and heavy cream.

Whip on high speed until light and fluffy.

Swirl pumpkin spice frosting onto cooled cookies.

Optional: finish with a light sprinkle of cinnamon.

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