Cut the roma tomatoes in half lengthwise. Using a small spoon, gently scoop out the seeds and most of the watery pulp from each half. This step is important - it prevents the tomatoes from steaming and helps them caramelize beautifully in the air fryer.
Place the tomato halves in a large bowl. Drizzle with olive oil, then add the minced garlic, Italian seasoning, salt, black pepper, and red pepper flakes. Toss gently until every tomato half is evenly coated.
Preheat the air fryer to 375°F for 2 minutes. Arrange the tomato halves cut-side up in a single layer in the air fryer basket - work in batches if needed so they aren't crowded.
Air fry at 375°F for 8 to 10 minutes, until the tomatoes are tender and the edges are lightly blistered and caramelized. The garlic should be fragrant and golden.
Sprinkle the grated parmesan cheese evenly over the cut side of each tomato half. Air fry for an additional 2 to 3 minutes, until the cheese is melted and turns a light golden brown.
Carefully transfer the tomatoes to a serving plate. Drizzle the balsamic glaze over the top in a zigzag pattern, then scatter the fresh basil over everything. Serve warm as a side dish alongside grilled meats, tossed into pasta, or piled on top of crusty bread.