Place the phyllo cups on a baking sheet and bake for 3 minutes; they are already baked, but this will give them a light crisp. Set aside and cool for 5 minutes.
Add the cream cheese, powdered sugar, milk, orange zest and vanilla to the bowl of an electric mixer fitted with a paddle attachment and whip together until light and fluffy, 1 to 2 minutes. Spoon the mixture into a pastry bag and set aside. Snip a small opening in the tip of the bag with a pair of scissors just before you are ready to fill the cups. No piping top needed.
Spoon 1/2 teaspoon of the cherry preserves into the bottom of each phyllo cup. Pipe a swirl of the cream cheese mixture into each cup, completely covering the preserves. Top each with a single raspberry and a mint leaf. Transfer them to a serving platter and give them a light dusting of powdered sugar.