Begin by straining 1 cup of whole milk ricotta to ensure a creamy filling without excess moisture. Place the ricotta in cheesecloth and squeeze out as much liquid as possible, discarding the excess.

In a mixing bowl, combine the strained ricotta with 1 cup of powdered sugar, ⅛ teaspoon of cinnamon, and ¼ cup of mini chocolate chips. Stir until the mixture is smooth and well combined. Set aside.

In a large mixing bowl or stand mixer, cream together ¾ cup of softened salted butter until light and fluffy. Gradually add ¼ cup of sugar and 1 cup of brown sugar, mixing until airy and pale in color. Then, incorporate 2 eggs and 1 teaspoon of vanilla extract. Blend until smooth.

Sift together 2 ¼ cups of flour, 1 teaspoon of baking soda, and ½ teaspoon of salt in a separate bowl. Gradually add this dry mixture to the wet ingredients, mixing on low speed until just combined. Gently fold in 1 cup of mini chocolate chips.

Preheat your oven to 350°F (175°C) and line your baking sheets with parchment paper.

Roll the chilled cookie dough into small balls, about 1.5 inches in diameter. Place them on the prepared baking sheets, spacing them apart. Flatten each ball and create a small well in the center using your thumb.

Spoon 1 tablespoon of the prepared ricotta filling into each well of the cookies. Chill the baking sheets in the refrigerator for 30 minutes to help the cookies retain their shape during baking.

Transfer the baking sheets to the preheated oven and bake for 14 minutes. Allow the cookies to cool completely on the baking sheets.

Dust your Cannoli Cookies with a light sprinkle of powdered sugar before serving.