Before you get started, be sure to drain your whole milk ricotta in cheesecloth for at least 6 hours.
Start with the cannoli shell bites so they have time to cool before garnishing the cupcakes.
Sift the flour, cinnamon, nutmeg and salt together in the bowl of a stand mixer, then add the sugar, stirring to combine.
Cut the butter into small cubes and add to the dry ingredients.
Mix on low until the butter is full incorporated (Additionally, a pastry blender would work well.).
Slowly add the Marsala, one tablespoon at a time, until the dough begins to come together in a ball.
Remove the dough from the bowl and knead for 2-3 minutes on a clean work surface.
Roll into a ball, then flatten into a disc and wrap in plastic wrap. Let the dough sit for an hour at room temperature.
After the dough has rested, heat 2-3 inches of canola oil in a high-walled pot until the oil hits 350-360 degrees Fahrenheit (use a candy thermometer).
As the oil heats, divide the dough into 4 portions. Take 1 portion (keeping the others wrapped up) and roll it out as thinly as possible. Use a round cookie cutter at least 3 inches wide and stamp out as many rounds as possible.
Once the oil is heated, add the cannoli rounds to the hot oil, letting them fry for 45 seconds to a minute before flipping them over with tongs. Fry until golden, then remove and place on paper towels to drain.
Repeat until all the dough is used up (you'll have extras, which are good for snacking).
Once the rounds have cooled, chop them up into bite-sized pieces.
If the cannoli bites are not as crisp as you'd like, place on a baking sheet and bake for 5 minutes at 350 degrees Fahrenheit.
Make sure cannoli shell bites are fully cooled before garnishing the cupcakes.
For the cupcakes, heat the oven to 350 degrees Fahrenheit and position the racks toward the center. Line pans with cupcake papers.
Combine the flour, baking powder, nutmeg and salt in a bowl and gently mix to combine. Set aside.
Cream the butter with the sugar, beating until light and fluffy.
Add the eggs one at a time, mixing to combine.
Alternate the dry ingredients and milk, and mix until combined.
Add the Marsala and vanilla extract, mixing to combine.
Divide the batter between 24 wrappers in the cupcake tins and bake for 20 minutes.
Cool completely on wire racks before frosting.
For the frosting, beat the butter and ricotta together on high for 5 minutes.
Add the sugar, and continue to beat.
If the texture looks a bit off (this can happen if you didn't drain it enough), add the cornstarch and continue beating on high for 5-10 minutes.
Using an extra large French tip (or your favorite piping tip), pipe the buttercream on top of the cooled cupcakes. Drizzle with chocolate, and garnish with some of the crushed cannoli bites.