First, Make The Pumpkin Cookies:

1. Preheat The Oven & Prep. 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.

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

3. Finish The Wet Ingredients. 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.

4. Add Dry Ingredients. 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.

5. Portion Out The Cookies. 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.

6. Bake & Shape. 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.

7. Cool & Repeat. 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. 

Then, Make The Cream Cheese Frosting:

1. Cream Butter & Cream Cheese. 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.

2. Add powdered sugar 1/2 cup at a time, mixing on medium-low speed until it’s fully added.

3. Finish Adding Ingredients. 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.

4. Whip The Frosting. 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.

5. Finish The Cookies. 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.

6. Store & Serve. 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.