1. Preheat the Oven

Preheat: Set your oven to 350°F (175°C) and line two baking sheets with parchment paper. This will help prevent the cookies from sticking and make cleanup a breeze.

2. Prepare the Cookie Dough

Cream Butter and Sugars: In a large mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy, about 2-3 minutes. This step is crucial as it incorporates air into the mixture, resulting in a lighter cookie.

Add Pumpkin and Eggs: Beat in the pumpkin puree, eggs, and vanilla extract until fully combined. The mixture should be smooth and creamy, showcasing the beautiful orange color of the pumpkin.

Mix Dry Ingredients: In another bowl, whisk together the all-purpose flour, baking powder, baking soda, salt, and spices. This ensures that the leavening agents and spices are evenly distributed throughout the dough.

Combine: Gradually add the dry mixture to the wet ingredients, mixing just until combined. Be careful not to overmix; you want to maintain the cookie’s tender texture.

3. Bake the Cookies

Scoop the Dough: Using a cookie scoop or tablespoon, drop rounded tablespoons of dough onto the prepared baking sheets, spacing them about 2 inches apart. These cookies will spread slightly during baking.

Bake: Bake in the preheated oven for 12-15 minutes, or until the edges are lightly golden and the centers appear set. Keep an eye on them to avoid overbaking.

Cool: Allow the cookies to cool on the baking sheets for about 5 minutes before transferring them to wire racks to cool completely. This will help them maintain their shape and texture.

4. Prepare the Glazes

Chocolate Glaze: In a microwave-safe bowl, combine the semisweet chocolate chips and vegetable oil. Heat in 30-second intervals, stirring in between, until melted and smooth. Let it cool slightly before using.

Vanilla Glaze: In a separate bowl, whisk together the powdered sugar and milk or heavy cream until smooth. Adjust the consistency as needed by adding more milk for a thinner glaze or more powdered sugar for a thicker glaze.

5. Glaze the Cookies

Once the cookies are completely cooled, it’s time to decorate!

Dip or Drizzle: Dip half of each cookie in the chocolate glaze, letting the excess drip off. For the vanilla glaze, either dip the other half or drizzle it over the top using a spoon or piping bag.

Let Set: Place the glazed cookies on a wire rack to let the glazes set completely. This will take about 30 minutes to an hour.