Step 1: Preheat the Oven

• Preheat your oven to 350°F (175°C) and grease a muffin tin or line it with paper liners.

Step 2: Make the Cookie Dough

• In a large mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
• Beat in the eggs one at a time, followed by the vanilla extract, mixing well after each addition.
• In a separate bowl, whisk together the flour, baking soda, and salt.
• Gradually add the dry ingredients to the wet ingredients, mixing until just combined. If using, fold in the chocolate chips.

Step 3: Bake the Cookie Cups

• Scoop about 2 tablespoons of cookie dough into each muffin cup, pressing down slightly to create a cup shape.
• Bake in the preheated oven for 10-12 minutes, or until the edges are golden and the centers are soft.
• Allow the cookie cups to cool in the pan for a few minutes before transferring them to a wire rack to cool completely.

Step 4: Prepare the Pudding Filling

• In a large bowl, whisk together the chocolate pudding mix, milk, and vanilla extract until smooth. Let it sit for about 5 minutes to thicken.

Step 5: Assemble the Cookie Cups

• Once the cookie cups are cool, fill each one with a generous scoop of chocolate pudding.
• Sprinkle the tops with crushed chocolate cookies to create a “dirt” effect.

Step 6: Decorate with Gummy Worms

• Finally, top each pudding cup with gummy worms and any additional Halloween-themed decorations you like.