Prep the chicken: Pat chicken cutlets dry. Season both sides with salt, pepper, Italian seasoning, and garlic powder.
Heat the pan: Set a large skillet over medium-high heat.
Add 1 tablespoon olive oil and swirl to coat.
Sear the chicken: Add chicken in a single layer. Cook 3–4 minutes per side until golden and nearly cooked through (internal temp about 160°F). Transfer to a plate and tent loosely with foil.
Sauté aromatics: Reduce heat to medium.
Add remaining 1 tablespoon olive oil and the minced garlic. Cook 30 seconds until fragrant, stirring to prevent burning.
Cook the tomatoes: Add tomatoes and a pinch of salt. Cook 2–3 minutes, just until they soften and release juices.
If you like heat, sprinkle in red pepper flakes.
Make it saucy: If using balsamic vinegar instead of glaze, pour 1/3 cup into the pan. Simmer 2–3 minutes until slightly reduced and syrupy. Stir in butter if using for a glossy finish.
Add back the chicken: Return chicken to the pan, nestling into the tomatoes.
Spoon some pan juices over the cutlets.
Top with mozzarella: Lay slices on each cutlet. Cover the skillet with a lid and cook 1–2 minutes, until the cheese melts and chicken reaches 165°F.
Finish and garnish: Drizzle balsamic glaze over the chicken (skip if you reduced vinegar in the pan). Scatter fresh basil on top.
Taste the juices and adjust salt and pepper.
Serve: Plate the chicken with tomatoes and pan sauce. Great with a side salad, buttered orzo, or crusty bread to soak up the juices.