For the Pumpkin Cookie Dough: Mix butter and sugars together to incorporate. Stir in egg and vanilla; mix until light and fluffy. Stir in pumpkin puree, then dry ingredients and spices until just incorporated. Scrape sides of the bowl and stir again briefly. Stir in caramel-filled chocolate chips by hand with a spatula. Refrigerate dough.
For the Double Chocolate Cookie Dough: Mix butter and sugars together to incorporate. Stir in egg and vanilla; mix until light and fluffy. Stir in milk, then dry ingredients until just incorporated. Scrape sides of bowl and stir again briefly. Stir in caramel filled chocolate chips by hand with spatula.
Remove pumpkin cookie dough from the refrigerator.
Line baking sheet with parchment paper or silicone baking mat. Using a 2 teaspoon-sized cookie scoop, scoop 12 level balls of pumpkin cookie dough out onto a prepared baking sheet. Using the same sized cookie scoop, do the same with the double chocolate cookie dough. Refrigerate 10-20 minutes until pumpkin cookie dough doesn't stick to your hands when touched.
Preheat oven to 350 degrees.
Once doughs have chilled together, push together gently to form a round cookie dough ball. Bake 8-10 minutes or until flattened and baked. The middle might seem slightly underdone but will finish cooking on the sheet. Once removed from the oven, cool 3 minutes on the hot pan before removing.
Serve warm. Cookies will keep in an airtight container for up to 3 days.