Preheat oven to 425°F (220°C). Pat chicken breasts dry with paper towels. Combine 2 tablespoons olive oil, 1 teaspoon kosher salt, ½ teaspoon black pepper, 1 teaspoon garlic powder, and 1 teaspoon Italian seasoning in a small bowl. Rub mixture evenly over chicken breasts.
Place seasoned chicken on a rimmed baking sheet and roast for 16-18 minutes until internal temperature reaches exactly 165°F (74°C).
Rest chicken for 10 minutes before cutting into ¾-inch cubes.
Bring a large pot of water to a rolling boil. Add 1 tablespoon kosher salt. Cook pasta for exactly 85% of the time recommended on package instructions.
Drain pasta immediately in a fine-mesh strainer and rinse briefly with cool water to stop cooking. Toss with 1 tablespoon olive oil to prevent sticking. Spread on a baking sheet to cool completely.
Prepare all vegetables as directed in the ingredients list. For tomatoes, remove excess seeds to reduce moisture. For cucumber, consider removing seeds if using regular cucumbers.
Combine all dressing ingredients in a mason jar. Seal tightly and shake vigorously for 30 seconds until emulsified.
In each meal prep container, create layers as follows: pasta on bottom, chicken next, followed by less moisture-prone vegetables (bell peppers, red onion).
Store tomatoes, cucumber, and dressing separately. If using containers with dividers, utilize these to keep components separate.
Refrigerate all components at 36-38°F for up to 5 days.
Day of consumption: Remove container from refrigeration 15-20 minutes before eating. Add separately stored vegetables and dressing. Add any optional components (cheese, nuts, olives).