Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper. Arrange the eggplant slices in a single layer on the sheet, brush both sides lightly with extra virgin olive oil, and season with salt and pepper. Roast for 10–12 minutes until pliable and soft with dark caramelized edges. Remove from the oven and cool slightly.

In a medium bowl, vigorously mix the ricotta cheese, egg, half of the shredded mozzarella (¼ cup), the grated Parmesan cheese, a pinch of salt, and pepper until completely smooth and uniform.

Spread 1 to 2 tablespoons of the plain basil pesto across the bottom of a rectangular 9x13-inch baking dish. Place a generous dollop (about 1.5-2 tablespoons) of the cheese filling onto one end of a roasted eggplant slice, press 2 to 3 cherry tomato halves into the cheese, and roll it up tightly. Place the roll seam-side down in the baking dish. Repeat for all remaining slices.

In a small bowl, mix the remaining pesto with 3 tablespoons of extra virgin olive oil. Drizzle this loose pesto mixture evenly over the tops of the rolls, allowing it to pool underneath. Scatter the remaining ¾ cup of shredded mozzarella cheese across the top. Bake at 400°F (200°C) for 18–22 minutes until the cheese is melted, golden-brown, and bubbling.

Remove from the oven and let rest for 3 minutes. Garnish with fresh basil ribbons (chiffonade) and serve warm, spooning the extra pesto oil from the bottom of the pan over the rolls.