Start by preheating the oven to 350 degrees F. Line two baking sheets with parchment paper or a macaron silicone baking mat (aka macaron silpat). Set out a medium cookie scoop or fit a piping bag with a large open tip for portioning out the pumpkin batter later.

In a large bowl, combine brown sugar and oil. Whisk until combined. (It will look like wet sand.)

Mix in pumpkin puree, then add eggs one at a time, mixing to fully incorporate each egg before adding the next one. Mix in the vanilla.

Next, add gluten-free flour blend, baking soda, baking powder, and salt, along with cinnamon, nutmeg, ginger, and cloves. Stir with a spatula until just combined (no floury patches left). Try not to over-mix the batter.

Using either a medium 2-Tablespoon scoop or a piping bag fitted with an open round tip, measure out the dough into 1.5 inch rounds onto the prepared baking sheet. If needed, use a just barely moist fingertip to smooth out any rough spots. I usually pipe out 9-12 cookies per batch.

Bake the cookies for 10-12 minutes, or until set all around and a toothpick inserted in the center comes out clean with just a few moist crumbs. (The tops of the cookies should spring back when gently pressed.) If desired, use a round cookie cutter to gently coax the cookies into a more perfect circular shape when they’re hot from the oven.

Cool 1-2 minutes on the baking sheet, then transfer to a wire cooling rack to cool completely. Repeat this baking process, alternating cookie sheets with each batch so you don’t put cool batter on a hot cookie sheet. Allow all cookies to cool completely before frosting.

Make sure the cream cheese and butter are softened to room temperature before combining, or they won’t blend well. In a large bowl or the bowl of a stand mixer fitted with a paddle attachment, combine softened cream cheese and butter. Mix together on medium speed with paddle attachment or a hand mixer for 1-2 minutes or until creamy and combined.

, mixing on medium-low speed until it’s fully added.

Scrape down the sides of the mixer, then add vanilla extract, a pinch of salt, 1 Tablespoon of heavy cream and either 1-2 Tablespoons of caramel sauce or pure maple syrup.

Mix on medium-high speed for 1-3 minutes or until smooth and fluffy. If the frosting seems too thin, you can add powdered sugar 1 Tablespoon at a time until it’s more stiff. If it’s too thick, you can add more heavy cream 1 teaspoon at a time to thin it out.

Flip over half of the cookies so they are bottom-side up/flat side up. These will be the base of your cookie sandwich. Pipe or spread frosting on the bottom cookies (flat side up), then top with a second cookie (flat side down) on top of the frosting to make a cookie sandwich.

Chill in the fridge until ready to serve. If desired, garnish with a sprinkle of powdered sugar right before serving. Store leftover pumpkin whoopie pies in an airtight container in the fridge up to 3 days, or freeze up to 2 months.