Preheat your oven to 450°F. While it heats, halve the sweet peppers and remove seeds, then peel the shallots and halve them lengthwise. Cut the top off each garlic clove to expose the flesh slightly, leaving the cloves unpeeled. Rinse the cherry tomatoes and pat dry. Arrange the peppers (skin-side up), shallots (cut-side up), and garlic cloves on a large baking sheet or roasting pan. Drizzle with 2 tablespoons of the Lucini Extra Virgin olive oil, sprinkle with kosher salt, and toss gently to coat.
Place the baking sheet in the preheated 450°F oven for 15 minutes. After 15 minutes, add the cherry tomatoes to the pan alongside the other vegetables and return to the oven. Continue roasting for another 10-15 minutes until the peppers are charred and tender, the shallots are caramelized and soft, and the garlic is golden and squeezable. The tomatoes will blister and soften during this time. Remove the pan from the oven and let cool slightly—I find a 5-minute rest makes it much easier to handle everything without burning your hands.
While the vegetables finish roasting, bring a large pot of salted water to a rolling boil and cook the penne according to package directions until al dente. Drain the pasta in a colander, rinse with cool water to stop the cooking process, and set aside. In the meantime, squeeze the roasted garlic cloves from their skins into a large mixing bowl. Add the lemon juice, 3.5 tablespoons of olive oil, honey, Italian herbs, Aleppo pepper, sea salt, and smoked paprika to the garlic. Whisk vigorously until the dressing is well combined and emulsified.
Once the roasted vegetables have cooled enough to handle, slice the peppers into 1/2-inch strips and cut the shallots into bite-sized pieces, discarding any charred outer layers if desired (though I actually prefer to keep them for the smoky flavor). Chop the sun-dried tomatoes into 1/2-inch strips if they aren't already. Stack the fresh basil leaves and thinly slice them into ribbons, and have the toasted pine nuts ready.
In a large bowl, combine the cooked pasta from Step 3 with the sliced roasted peppers and shallots, sun-dried tomatoes, and fresh basil ribbons from Step 4. Pour the dressing from Step 3 over the pasta and vegetables, then toss everything together until well coated and evenly distributed. Sprinkle the toasted pine nuts over the top and gently toss once more to incorporate them, reserving a small handful for garnish if desired. Taste and adjust seasoning as needed—I like to add an extra pinch of Aleppo pepper for a subtle heat boost if the dish needs more punch.