Preheat your oven to 400°F (200°C). Place an ovenproof skillet or tart pan over medium heat and add a tablespoon of butter. Once melted, sprinkle the sugar evenly over the butter and let it cook until it begins to caramelize and turn golden, about 2-3 minutes, filling the kitchen with a warm, sweet aroma.
Arrange the tomato halves cut side down in the caramelized sugar mixture in a single layer, overlapping slightly if needed. Cook for about 10 minutes, until the tomatoes start to soften and release their juices, which meld with the caramel.
Remove the skillet from heat. Roll out the puff pastry on a lightly floured surface to fit slightly larger than the skillet's diameter. Carefully place the pastry over the tomatoes, tucking the edges around the sides of the skillet.
Bake the tart in the preheated oven for 25-30 minutes, or until the pastry is puffed and golden brown. The tomatoes will become tender and the caramel will turn rich and syrupy.
Once baked, remove the skillet from the oven. Let it rest for 5 minutes to allow the caramel to set slightly. Then, carefully invert the tart onto a serving plate, revealing a glossy, caramel-coated top with roasted tomatoes.
Gently lift the skillet and place it back on the counter. Garnish with a pinch of sea salt and freshly ground black pepper for enhanced flavor. Serve the Tomato Tarte Tatin warm as a savory appetizer or main dish, enjoying the tender, caramelized tomatoes surrounded by flaky pastry.
