Halve the cherry tomatoes and spread them on a baking sheet lined with parchment paper. Drizzle with 1 tablespoon of olive oil, and sprinkle with oregano, pepper, and grated garlic. Bake at 350°F (180°C) for about 20 minutes, or until slightly dehydrated and their flavor has concentrated.
Drain the mozzarella and cut it into small cubes. Let the roasted tomatoes cool slightly, then mix with the cheese. Tip: Do not mix while the tomatoes are too hot, or the mozzarella will melt and be difficult to portion.
Cut the filo pastry into long strips. Place a tablespoon of the tomato-cheese filling at the end of each strip, then fold it up in a triangular shape. Seal the ends with water to prevent them from opening during baking.
Place the samosas on a baking sheet lined with parchment paper, then brush the tops with the remaining olive oil. Bake in a preheated oven at 390°F (200°C) for 15-18 minutes, or until golden brown and crispy. Tip: Watch to make sure the cheese doesn't ooze out of the edges.
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