If you've ever eaten a baked penne dish, you know what the best part is: the crispy pasta around the edges! Now imagine if you had a whole plate of those brown, crispy-yet-tender pasta pieces. Wonder no more with this pan-fried penne dish. Cooked pasta gets lightly browned and topped with zesty tomato sauce for an experience so satisfying, plain boiled pasta might not cut it anymore.
Cut end off romaine, halve lengthwise, then coarsely chop. Mince garlic. Cut cauliflower florets into even, bite-sized pieces no larger than 1".
Roast Cauliflower and Make Caesar Dressing
Place cauliflower florets on prepared baking sheet. Drizzle with 2 tsp. olive oil and season with a pinch of salt and pepper. Roast 12 minutes or until almost tender. Remove from oven, sprinkle with half the Parmesan, and roast 7 more minutes, or until cheese browns lightly. In a large mixing bowl, whisk mayonnaise, vinegar, half the garlic, and remaining Parmesan (reserving a pinch for garnish). Season to taste with salt and pepper and set aside.
Cook the Pasta
Add penne pasta to boiling water and cook 9 minutes until al dente. Before draining, reserve ½ cup pasta cooking water for sauce. Drain pasta in colander, being sure to drain as thoroughly as possible. While in colander, drizzle and toss pasta with 2 tsp. olive oil to keep from sticking. Return pot to stove (no need to wipe clean.)
Make the Arrabiata Sauce
In pot used to cook pasta, heat 1 tsp. olive oil over medium-high heat. Add remaining garlic and red pepper flakes (a little goes a long way with red pepper flakes, so use less if you prefer a milder sauce) and cook 20 seconds until fragrant. Add Italian seasoning and tomato paste and cook 1 more minute. Add crushed tomatoes and reserved pasta water, bring to a simmer, and cook 5-8 minutes until thickened slightly. Set aside and keep warm.
Pan Fry the Pasta
Heat 2 tsp. olive oil in a large non-stick pan over medium-high heat until oil is hot and shimmering. Working in batches, add a single layer of pasta to pan. Allow to cook undisturbed for 3-4 minutes. Not moving pasta around allows it to brown and develop a highly desirable crispness. After underside has browned, stir gently and cook 3 more minutes, stirring occasionally. Don't worry if pasta only browns on one side: two different textures are ideal. Keep finished batches warm on baking sheet in oven.
Plate the Dish
Place a pool of arrabiata sauce on bottom of plate. Top with pan-fried penne and roasted cauliflower. Top with one more spoonful of sauce and remaining Parmesan. Toss romaine lettuce with Caesar dressing and serve salad on the side.