Preheat your oven to 400°F. While it heats, prepare all vegetables: cut bell peppers into 1-inch squares, halve the cherry tomatoes, slice zucchini and yellow squash into 1/2-inch thick half-moons, and cut red onion into 1-inch chunks. In a large bowl, toss all vegetables with 3 tablespoons olive oil, kosher salt, red pepper flakes, and cracked black pepper until evenly coated. Spread vegetables in a single layer on a large baking sheet (I prefer to use two sheets if needed rather than crowding them, as this ensures better caramelization). Roast for 10 minutes, give everything a good stir, then roast for another 5-10 minutes until the vegetables are tender with lightly caramelized edges.
While the vegetables roast, bring a large pot of salted water to a boil. Add orzo and cook according to package directions until al dente, usually about 9-11 minutes. Drain the orzo in a colander and set aside. I like to leave it slightly warm so it absorbs the dressing flavors more effectively.
In a jar or bowl, whisk together extra virgin olive oil, balsamic vinegar, pressed garlic, Dijon mustard, dried basil, dried oregano, fresh lemon juice, salt, and black pepper. Whisk vigorously until the dressing is well emulsified and the flavors are fully combined. Taste and adjust seasonings as needed—I often add an extra squeeze of lemon juice if I want more brightness.
In a large mixing bowl, combine the cooked orzo from Step 2 with the roasted vegetables from Step 1. Pour the vinaigrette from Step 3 over the warm salad and toss gently but thoroughly until everything is well coated and the flavors are evenly distributed. Let the salad sit for a few minutes before serving to allow the warm pasta and vegetables to fully absorb the dressing flavors.