Preheat oven to convection 350 degrees Fahrenheit 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 (1–2 minutes).

Mix in egg and vanilla extract until smooth.

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

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

Crush Oreos by hand or in a food processor.

In a small bowl, mix together brown sugar, crushed Oreos, and canned pumpkin until combined.

Scoop ~⅓ cup of cookie dough and flatten slightly in your hand. Add 1 tsp of the Pumpkin Oreo mixture into the center, then fold dough around it and roll into a ball.

Place cookie dough balls on the prepared tray, leaving space between each.

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

Optional: For perfectly round cookies, use a circular cookie cutter or glass to gently swirl around each fresh cookie as soon as it comes out of the oven.

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

In a stand mixer, beat butter until creamy and pale. Add powdered sugar gradually until incorporated.

Mix in drained pumpkin (drain using a cheesecloth), pumpkin pie spice, salt, cinnamon, and heavy cream. Whip on high speed until light and fluffy.

Add more oreo mixture on top (optional) and swirl pumpkin spice frosting on top of oreo mixture.

Optional: sprinkle with extra crushed Oreos for garnish.

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