Preheat your oven to 375°F (190°C).

Line two baking sheets with parchment paper and set them aside.

In a large mixing bowl, combine the melted and cooled butter, light brown sugar, and granulated sugar.

Stir until the mixture is smooth and the sugars are evenly incorporated.

Add the pumpkin puree, lightly beaten eggs, and alcohol-free vanilla extract.

Mix thoroughly until the ingredients form a smooth, evenly blended mixture.

In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, salt, pumpkin pie spice, and ground cinnamon.

Make sure the spices and leavening agents are evenly distributed throughout the flour.

Gradually add the dry ingredients to the pumpkin mixture.

Stir gently until everything is combined and the batter is smooth.

Avoid overmixing, as this can make the finished cookies less tender.

Using a rounded tablespoon or small cookie scoop, portion the batter onto the prepared baking sheets.

Leave at least 2 inches between each scoop to allow room for spreading.

Try to keep the portions similar in size so the cookies bake evenly and pair neatly when assembled.

Bake for approximately 9 minutes, or until the cookies appear set and spring back lightly when touched.

Remove the baking sheets from the oven and allow the cookies to cool completely before adding the frosting.

In a medium mixing bowl, beat the softened butter and cream cheese together using an electric mixer.

Mix until the filling becomes smooth, creamy, and free of lumps.

Gradually add the powdered sugar, beginning with 2 cups and increasing the amount as needed to achieve a thick, spreadable consistency.

Add the alcohol-free vanilla extract and salt, then mix until fully incorporated.

Pair the cooled pumpkin cookies according to size.

Pipe or spread a generous layer of cream cheese frosting onto the flat side of one cookie.

Place a second cookie on top, flat side down, and press gently to create a sandwich.

Repeat with the remaining cookies and frosting.

Serve your Pumpkin Whoopie Pies immediately, or refrigerate them briefly to help the frosting firm up.

For the softest texture and creamiest filling, allow refrigerated whoopie pies to sit at room temperature for about 10–15 minutes before serving.