In a food processor, add in the 12 Store-bought Gingerbread Soft Cookies. Pulse on low until all of the cookies are crumbs.
Add in the 1/4 cup whole milk and continue to pulse for about 1 minute until the mixture is smooth. Scrape down the sides of the bowl if needed.
Add in the 8 ounces cream cheese, 1 1/2 tablespoons molasses, 1 teaspoon ground cinnamon, 1 teaspoon ground ginger, and 1/3 cup powdered sugar. Pulse on low until the cream cheese is thoroughly incorporated and the mixture is smooth and creamy. Stop and scrape down the bowl to get any bits that are stuck to the sides of the food processing bowl. Pulse to blend in any remaining bits.
Scoop the mixture out of the food processor into a medium mixing bowl.
Add the thawed 8 ounces whipped topping to the mixture and fold in with a spatula.
Scoop into a serving bowl, sprinkle with red and green sanding sugar, and top with another gingerbread cookie.
Place in the fridge to chill for at least 1 hour before serving. This will allow the mixture to thicken up slightly.
Store in an airtight container or wrapped with plastic wrap in the refrigerator.
Notes
Storage: Store covered or in an airtight container in the refrigerator for up to 5 days.