Preheat your oven to 180°C (350°F) and line baking sheets with parchment paper. This prepares a warm, ready surface for baking.
In a large bowl, whisk together the flour, baking soda, and salt until evenly combined. This creates a dry mixture that helps the cookies rise evenly.
In another bowl, beat the softened butter and brown sugar with an electric mixer or whisk until the mixture is light, fluffy, and fragrant, about 2-3 minutes.
Add the pumpkin puree and vanilla extract to the butter and sugar mixture, mixing until well incorporated and smooth. The mixture should look moist and slightly thick.
Gradually add the dry ingredients to the wet mixture, mixing just until combined. The batter will be thick but scoopable, with a soft, dough-like texture.
Using a cookie scoop or spoon, portion out 1 1/2-inch rounds of dough onto the prepared baking sheets, spacing them about 2 inches apart to allow for spreading.
Bake in the preheated oven for 12-15 minutes, until the edges are golden and the centers are set. The cookies will look slightly puffy and firm around the edges.
Remove the cookies from the oven and transfer them to a cooling rack. Let them cool completely, which allows the texture to firm up and makes them easier to handle.
In a separate bowl, beat the softened cream cheese and powdered sugar until smooth and creamy, about 2 minutes. This creates a tangy, luscious filling.
Once the cookies are cool, spread or pipe a generous dollop of the cream cheese filling onto the flat side of one cookie, then top with another cookie to create a sandwich.
Press gently to secure the filling and enjoy these soft, spiced pumpkin whoopie pies that combine warm aromas with a tender, chewy texture.
