Grab a medium bowl. Whisk the cooled butter, granulated sugar, and brown sugar until smooth and lump-free. Stir in the blotted pumpkin and vanilla until everything combines well. Set that bowl aside.
Whisk the flour, baking soda, baking powder, cinnamon, salt, and pumpkin pie spice in another larger bowl. Pour the wet mixture (from Step 1) into these dry ingredients and stir until creamy.
Fold in half a cup of chocolate chips.
Once your dough is ready, cover it and put it in the fridge to chill for at least 30 minutes. If you plan ahead, you can even leave it there for 2-3 days.
Preheat your oven to 350°F (or 177°C) when ready to bake, and line your baking sheets with silicone mats or parchment paper.
Grab your chilled cookie dough. Scoop about 1 ½ tablespoons per cookie, rolling each into small balls. Space them on your baking sheets, about 2 to 3 inches apart. Gently flatten their tops with a cup or a small spoon.
Bake them for 11 to 12 minutes until the edges are nice and set. Their centers might still look soft.
Let them out of the oven. Flattening them with a spoon should do the trick if they don't spread much. Optional: Press some chocolate chips onto these warm cookies.
Let the baked cookies sit on your baking sheets for 10 minutes (or longer), then move them to a rack to chill completely. If you leave them for a few hours at room temperature, they will be even chewier and more pumpkin-y on day two. Enjoy!