Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper and set aside. This step ensures your equipment and oven are ready for baking once the batter is made.

In a medium bowl, whisk together the all-purpose flour, baking powder, baking soda, kosher salt, cinnamon, ground cloves, nutmeg, and ground ginger until thoroughly combined. In a separate glass measuring cup or small bowl, combine the whole milk, vegetable oil, 1 teaspoon vanilla extract, and pumpkin purée, mixing well until smooth. Set both mixtures aside to use in later steps.

In the bowl of a stand mixer fitted with the paddle attachment, cream together 3/4 cup unsalted butter (room temperature), white sugar, and brown sugar on medium speed until the mixture is lighter in color and fluffy. Add one egg, beating on medium-low speed until fully combined. Scrape the bottom and sides of the bowl, then repeat with the second egg, ensuring everything is well-incorporated.

With the mixer on low speed, add one-third of the dry ingredient mixture (from Step 2) to the creamed butter and egg mixture (from Step 3). After it incorporates, pour in half of the wet pumpkin mixture (from Step 2). Alternate adding the remaining dry and wet mixtures, starting and ending with the dry mixture. Mix only until the last bits of flour disappear, then turn off the mixer and gently stir to ensure everything is fully combined, scraping down the sides and bottom. Do not over-mix. I like to give the batter one last gentle fold by hand to avoid overworking the gluten for soft, tender whoopies.

Using a 1/4-cup muffin or cookie scoop, portion out six rounds of batter per prepared sheet, keeping them as circular as possible. Use a spoon to help shape if needed. Bake for 16 minutes, rotating and switching the trays halfway through for even baking. The edges should be slightly browned and the tops should spring back when gently touched, even if pale. Let them cool on the baking sheets for 3 minutes, then transfer to a wire rack to cool completely. Repeat with the remaining batter.

In a stand mixer fitted with the paddle attachment, cream together 1 cup unsalted butter (room temp) and 1 cup confectioners’ sugar until light in color and fluffy. Add the cream cheese or mascarpone (room temp) and 1 teaspoon vanilla extract, beating until smooth and combined. Scrape down the bowl, then add another cup of confectioners’ sugar and a pinch of kosher salt. Beat at medium speed until the mixture comes together, then turn the mixer to low and let it run for about three minutes to eliminate air bubbles and achieve a creamy filling. For even more flavor, I sometimes add a tiny splash of lemon juice to brighten up the filling.

Using a piping bag fitted with a circular tip, or a resealable plastic bag with the corner snipped off, pipe the cream cheese or mascarpone filling onto half of the cooled whoopie pies. Top each filled half with a plain pie to make a sandwich. Serve and enjoy!