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For the phyllo dough cups:
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Preheat oven to 350 F. Spray a standard 12-count muffin pan with cooking spray; set aside.
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Layer 3 phyllo sheets on your cutting board, lightly spraying each sheet with cooking spray. Cut the stack into 8 equal squares (so you'll have 8 squares with 3 sheets of phyllo dough). Place each stack of cut squares into the standard muffin pan.
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Carefully push the dough stack into the pan, pressing firmly against bottom and sides.
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Repeat the stacking and cutting process 1 more time with the remaining 3 sheets of dough. You'll use 4 more stacks of dough to make 12 tarts (you'll have some dough leftover).
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Bake empty shells in the oven for 8-10 minutes or until golden brown. Remove pan from oven and set it on a rack. Cool for 5 minutes. Remove shells from pan.
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To make the cannoli filling:
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In the bowl of a stand mixer with the paddle attachment, add ricotta cheese and mascarpone cheese and blend until light and fluffy, about 2-3 minutes. Add sugar, almond extract and maraschino cherry juice. Mix until incorporated and filling is light and fluffy, about 7 minutes total time.
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Add cannoli filling to phyllo cups, sprinkle with pistachios and top with a cherry.
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Note: Fill the cups with cannoli mix when ready to use, otherwise the cups will get soggy. Store cups in a sealed container at room temperature.