Preheat the oven to 350°F. Line two sheet pans with parchment paper and set aside.: The air in your oven will gradually warm and the aroma of baking will begin to build, signaling the start of the transformation. You should hear the faint hum of the oven elements and feel a steady, even heat if you open the door carefully. Accurate oven temperature matters for even rise and proper setting of the cookies, so use an oven thermometer if your oven tends to run hot or cold. A common mistake is placing pans before the oven reaches temperature, which can lead to flatter cookies.
Use a mixer to beat the light brown sugar and butter together until creamy and fluffy. Add in one egg and beat until fully combined and then add the other egg. Be sure to scrape down the sides to ensure everything is mixed.: As you whip the brown sugar with the softened butter , you will notice the mixture lighten in color and become airy, creating tiny pockets that help the cookies rise. After adding each egg , the batter should look smooth and cohesive, and scraping the bowl prevents pockets of unmixed butter or sugar. This stage is essential for texture and even baking. Avoid overbeating after the flour is added, because that can develop gluten and make cookies tough.
Beat in the pumpkin puree.: When you add the pumpkin , the batter will loosen and take on a rich, rust colored hue. The scent of autumn spices and pumpkin will grow more pronounced, and the batter should feel moist but not runny. Stir gently until uniform, being careful not to overwork the mixture. If the batter becomes too slack, resist adding too much flour; instead check your measuring technique or chill the bowl briefly before scooping.
In a separate, large bowl whisk together the all-purpose flour, pumpkin pie spice, baking soda, and baking powder.: Whisking these dry elements distributes the pumpkin pie spice and leaveners evenly so each scoop has the same balance of flavor and lift. The dry mix will smell warmly spiced, and you should see a consistent color throughout. If you skip this step, you risk uneven pockets of baking soda or spice, which can cause irregular rise or bitterness.
Beat the flour mixture in with the butter mixture. Mix until fully combined but do not overmix.: As the dry ingredients fold into the wet, the batter will thicken and the texture will transform into a soft, scoopable dough. You should stop mixing as soon as you see no streaks of flour, because excess stirring develops gluten and yields chewier cookies instead of tender ones. A common error is overmixing while trying to smooth the batter, so finish by hand if needed to avoid overworking.
Use a medium cookie scoop to scoop mounds of batter onto the prepared sheet pans. Leave about 2-inches between each cookie.: Scooping creates uniform cookies that bake evenly and match up nicely when paired. You will notice the batter holds its shape but has a slightly domed top; spacing them allows for gentle spreading without sticking. If your scoops vary widely in size, the smaller ones will bake faster and can overbrown, so keep a steady hand or use a scale for precision.
Bake in the oven for 12-15 minutes or until the middle sets. Remove from the oven and let the cookies cool completely.: During baking you will see the edges set and the centers spring back slightly when touched, and the scent of spices will intensify. Proper bake time ensures the cookies are cooked through but remain soft. Letting them cool fully is crucial because a warm cookie can compress and cause the filling to melt. Taking them out too early leads to underbaked centers, while overbaking will dry them out.
To make the filling, beat the salted butter and cream cheese until fully combined and creamy. Gradually beat in the powdered sugar, heavy cream, and salt until light and fluffy, about 5 minutes.: As you whip, the filling will become velvety and pale, with a faint sheen and a cloud like texture. The cream cheese tang cuts through the sweetness of the powdered sugar , and the heavy cream helps achieve a smooth, pipeable consistency. If the filling seems too thin, chill briefly and rewhip; if too thick, add a splash more cream. A frequent mistake is adding the sugar too quickly, which can make the filling gritty.
To assemble the pies, take one cookie and pipe filling onto the bottom of the cookie. Top with another cookie and refrigerate until ready to serve.: When assembled, the filling should be visible but not overflowing, creating a neat sandwich that is pleasing to hold and eat. Press gently to spread the filling evenly to the edges; the contrast of the soft cookie and creamy center is the signature of these pies. Refrigerating helps the filling firm so the pies slice cleanly and transport easily. Avoid stacking while still warm, as the filling can squish out and become messy.