Preheat your oven to 375 degrees F and line one cupcake pan with paper liners.
Add the flour, sugar, baking powder, and salt to a large mixing bowl. Whisk until combined.
Add the vegetable oil, milk, eggs, and vanilla to the dry ingredients. Continue to whisk until the batter comes together and is smooth. Don't overmix.
Fill each cupcake liner about ¾ full with the cake batter.
Place in the preheated oven and bake for 18-20 minutes or until a toothpick inserted into the center comes out clean.
Let the cupcakes cool for about 10 minutes before transferring them to a wire rack to cool completely.
Add the ricotta, powdered sugar, and vanilla to a small bowl. Whisk until combined.
Add the chocolate chips and cinnamon. Stir until the chocolate chips are evenly distributed. Set aside until ready to use.
Add the butter and mascarpone to a large mixing bowl. Beat using a hand mixer on medium speed until creamed.
Add the powdered sugar and vanilla extract. Continue to mix until the powdered sugar is incorporated. Turn the mixer to high and beat until whipped, about 1 minute.
Add the frosting to a piping bag fitted with the Wilton 1M piping tip.
Assemble the Cannoli Cupcakes
Cut a small hole out of the center of each cupcake using a paring knife or apple corer. Be sure to not cut all the way through the cupcake.
Fill each cupcake with 1 tablespoon of cannoli filling and place the top of the cake back on top of the cannoli filling.
Pipe the frosting on top and garnish with additional mini chocolate chips or a filled mini cannoli.
Store any leftover cupcakes in an airtight container in the fridge.
For a thicker Cannoli Filling, drain the ricotta in a fine-mesh strainer overnight before using it. If you want to top each cupcake with a mini cannoli, I recommend doubling the frosting recipe. You can mix mini chocolate chips into the second half of the recipe and pipe into the mini cannoli shells.