Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.
In a medium mixing bowl, combine the softened cream cheese, cheddar, parmesan, garlic, parsley, and black pepper. Mix until smooth and well combined. If the mixture feels too thick, add a teaspoon of milk to loosen it slightly.
Arrange the phyllo shells on the prepared baking sheet. Lightly brush the top edge of each shell with olive oil to help them brown evenly.
Spoon approximately 1/2 teaspoon of the cheese mixture into each shell. Do not overfill, as they will puff up slightly.
Bake for 8-10 minutes, or until the shells are golden brown and the filling is bubbly. Keep a close eye on them after minute 7, as phyllo can burn quickly.
Remove from the oven and let cool for 2 minutes before serving. They are best served warm.