Step 1: Preheat Your Oven

Begin by preheating your oven to 350°F (175°C). Line two baking sheets with parchment paper to prevent sticking.

Step 2: Mix the Dry Ingredients

In a medium bowl, whisk together the flour, baking soda, and salt. If you’re using pumpkin spice, add it in as well. This ensures an even distribution of the leavening agent.

Step 3: Cream the Butters and Sugars

In a large mixing bowl, beat the softened butter, granulated sugar, and brown sugar together until light and fluffy, about 3-4 minutes. This is a crucial step for a soft, chewy texture.

Step 4: Add Eggs and Vanilla

Add the eggs, one at a time, mixing well after each addition. Then, stir in the vanilla extract until fully combined.

Step 5: Combine Wet and Dry Ingredients

Gradually add the flour mixture to the butter mixture, mixing just until combined. Be careful not to overmix, as this can lead to tough cookies.

Step 6: Prepare the Chocolate Filling

Using a small cookie scoop or tablespoon, portion out the milk chocolate chips. Set them aside; you’ll be using them in the next step.

Step 7: Shape the Cookies

Using a tablespoon of cookie dough, flatten it in your palm and place a few chocolate chips in the center. Then, wrap the dough around the chocolate, rolling it into a ball. Make sure the chocolate is fully enclosed.

Step 8: Place on Baking Sheet

Arrange the cookie dough balls on the prepared baking sheets, leaving space between each one for spreading.

Step 9: Bake the Cookies

Bake in the preheated oven for 10-12 minutes or until the edges are lightly golden. The centers may look slightly underbaked, but they’ll firm up as they cool.

Step 10: Cool the Cookies

Allow the cookies to cool on the baking sheet for about 5 minutes before transferring them to wire racks to cool completely.

Step 11: Decorate Your Cookies

Once the cookies are completely cool, it’s time to decorate! Using orange icing, pipe jack-o’-lantern faces on the cookies. Use green icing for the pumpkin stems. If you want to add candy eyes, now’s the time!

Step 12: Enjoy!

Your Milk Chocolate Stuffed Jack-O’-Lantern Cookies are now ready to be enjoyed! Serve them at your Halloween party or share them with friends and family.