In the bowl of a stand mixer fitted with a whisk attachment, whip the cream until stiff peaks form. Place the cream into a small bowl and set aside.
In the same mixing bowl, add the ricotta cheese, powdered sugar, vanilla, and cinnamon. Mix on medium speed until well combined, about 1 minute. Fold in the whipped cream and chocolate chips.
Chill the cream for at least 2 hours before filling the cannoli shells.
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Notes
This recipe makes about About 2 1/2 cups of cannoli filling. You will need about 2 tablespoons of cannoli filling to fill each small cannoli. This will make enough filling to fill 20 small and 12 large cannoli. This recipe calls for strained ricotta cheese. Check out my How to Strain Ricotta Cheese tutorial.