Preheat the Oven: Preheat your oven to 350°F (175°C) and grease a mini muffin tin.
Prepare the Cookie Dough: In a mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy. Add the egg and vanilla extract, mixing until combined.
Combine Dry Ingredients: In a separate bowl, whisk together flour, baking soda, and salt. Gradually add this dry mixture to the butter mixture, mixing until just combined.
Form the Cookie Cups: Roll dough into 1-inch balls and place each ball in a mini muffin tin. Gently press down in the center of each ball to form a cup shape.
Bake: Bake for 10-12 minutes, or until the edges are golden. Once baked, use the back of a spoon to press down the centers again, reinforcing the cup shape. Let the cookie cups cool completely in the tin.
Prepare the Cannoli Filling: In a medium bowl, whisk together ricotta, mascarpone, powdered sugar, vanilla extract, and cinnamon until smooth. Fold in mini chocolate chips.
Fill and Serve: Spoon or pipe the cannoli filling into each cooled cookie cup. Garnish with extra mini chocolate chips if desired. Serve immediately or refrigerate until ready to serve.