In a medium bowl, mix together 2 and ½ cups of flour, baking powder, salt, pumpkin pie spice, and cinnamon. Set the mixture aside.
In a large bowl, use a hand mixer or stand mixer with the paddle attachment to beat the butter and confectioners' sugar until the mixture is light and fluffy, which should take about 3 minutes.
Beat the egg with both extracts in a small bowl or measuring cup. Add this egg mixture to the creamed butter and sugar, beating on high until well combined, scraping the sides as needed.
Gradually add the flour mixture to the wet ingredients on low speed, allowing the dough to come together after each addition. Once all the flour is mixed in, the dough should stick to your beaters or paddle.
Test the dough's consistency by touching it. It should be slightly tacky but not sticky, similar to Play-Doh. If it's too sticky, incorporate 2 to 4 tablespoons of flour at a time until reaching a total of 3 cups of flour (adding two increments). Be cautious not to exceed this amount as too much flour will make the cookies dense.
Once the dough is properly mixed, form it into a ball and let it rest for 10 minutes. During this time, preheat your oven to 400ºF (204ºC) and line two large baking sheets with parchment paper or silicone mats.
Lightly dust your rolling surface with confectioners' sugar. If desired, use two ¼" wooden dowels on either side of the dough to maintain an even thickness while rolling.
Roll out the dough into a workable size, typically dividing it into 4 portions. Roll with a sugared rolling pin and cut into shapes with cookie cutters. Dip the cutter in confectioners' sugar to keep edges clean.
Place the cut dough on baking sheets, ensuring cookies of similar sizes are grouped together for even baking. Re-roll and cut remaining dough as needed. Decorate with sprinkles or icing later if desired.
Bake cookies for 4-6 minutes. Medium cookies (2") need about 6 minutes, while mini cookies (1") take about 4 minutes. Remove from the oven when slightly puffed and no longer shiny. Edges might begin to brown; this is acceptable. Let cookies rest on the baking sheet for 5 minutes before transferring to a wire rack to cool completely. Decorate day-old cookies for better sturdiness if preferred. Undecorated cookies can be frozen for up to 3 months; thaw overnight before decorating.
For Pumpkin Spice Cookie Icing:
x confectioners' sugar and pumpkin pie spice in a medium bowl. In a separate small bowl, combine warm water, light corn syrup, and pumpkin spice extract, stirring until the corn syrup is dissolved.
Add the sugar mixture to the liquid ingredients and stir until smooth. The icing should have a slow drip consistency, disappearing into the bowl in about 12 seconds. Adjust thickness with additional water or confectioners' sugar as needed. Use immediately or cover tightly for up to 1 day, stirring before use. Store decorated cookies in an airtight container at room temperature.