In a medium sized bowl, toss together 2 and ½ cups of flour, baking powder, salt, pumpkin pie spice, and cinnamon. Set aside.
In a large bowl with a hand mixer or the bowl of a stand mixer with the paddle attachment, cream together butter and powdered sugar until light and fluffy, about 3 minutes. In a measuring cup or small bowl with a spout, beat the egg and extracts. Add egg mixture to creamed butter and sugar and beat on high until completely incorporated, scraping down sides as necessary.
With mixer on low, add flour mixture to wet ingredients little by little, allowing dough to come together after each addition. After you have added all 2 and ½ cups of flour (plus baking powder and salt) to the bowl, most of the dough should stick to your beaters or paddle.
Test dough consistency by touching it with your fingers. It should be slightly tacky, but not sticky. It should remind you of Play-Doh. If it is too sticky, add ¼ cup of flour at a time until you reach 3 total cups of flour (two additions). Occasionally, I will need a tad more flour, but do not exceed 3 cups + 2 Tablespoons flour. Too much flour yields denser cookies, and we want these to stay soft. When your dough is the right consistency, gather it into a ball and allow it to rest for 10 minutes. While it is resting, preheat your oven to 400ºF. Line two large baking sheets with parchment paper or silicone baking mats. Set aside.
Prepare your rolling surface by dusting it lightly with powdered sugar. If you would like, use two wooden dowels, sized at ¼" thickness, on either side of your dough while rolling it out to keep cookies a uniform thickness.
When your dough is ready to roll, break off a workable size of dough. I usually break it into 4 pieces. Roll dough with a powdered sugared rolling pin and cut into desired shapes with cookie cutters. I like to dip my cookie cutter into powdered sugar every few cuts to keep my cookie edges clean. Transfer cut dough onto baking sheets. It is best to keep cookies that are the same size and shape together on baking sheets so as to uniformly bake all of your cookies. Re-roll and cut dough as needed until all of the dough is used up. At this point, you may decorate cut cookies with sprinkles or just leave them plain and decorate them with icing later.
Bake cookies for 4-6 minutes. Medium cookies (2") take about 6 minutes. Mini cookies (1") take about 4 minutes. Bake until cookies are slightly puffed and are no longer shiny. Edges may start to brown, and that's ok, just work quickly to remove them from the oven. I prefer to remove mine before they start to brown. Allow cookies to rest on baking sheet for 2 minutes before transferring to wire rack to cool completely. I prefer to decorate day-old cookies, as they are sturdier, but this is personal preference and only a suggestion. Undecorated cookies freeze extremely well (I actually like to eat them frozen!), up to 3 months. Do not freeze decorated cookies. Thaw overnight before decorating previously frozen cookies.
PUMPKIN SPICE COOKIE ICING*
When you're ready to decorate your cookies, place powdered sugar and pumpkin pie spice in a medium bowl and set aside. In a small bowl, combine warm water, light corn syrup, and pumpkin spice extract. Stir until corn syrup is dissolved.
Add sugar water to powdered sugar and stir until completely combined. Mixture will be thick. The consistency you're looking for is a slowly dripping icing that disappears into the bowl within about 12 seconds. Add water by drop if you think it's too thick. If it becomes too thin, add more powdered sugar by the teaspoon. Use immediately. If you need to wait to use your icing, cover tightly, and use within 1 day. You will need to stir it up again and possibly add more water before using. Cookies will stay fresh in an airtight container at room temperature well over a week.
Start with 2 and ½ cups of flour and work your way up to 3 cups as needed. Do not exceed 3 cups + 2 Tablespoons.
Room temperature egg preferred. It is always a good idea to use a room temperature egg when using room temperature butter, which allows for better incorporation into dough.
*See my detailed easy royal icing recipe for a video of exactly how to make this icing and what the drizzle test looks like.