Preheat oven to 400 degrees F.: You will feel warmth starting to radiate from the oven as it approaches the correct heat, and the internal fan may hum gently. A fully heated oven ensures the tomatoes blister quickly rather than steam, which is crucial for developing their concentrated, sweet flavor. If the oven is not hot enough, the tomatoes will release juice and become soggy instead of blistered. Be sure to place the rack in the center position for even roasting.
Place tomatoes along with 2 teaspoons olive oil in a baking dish. Sprinkle with half the salt & pepper.: As the tomatoes hit the hot dish, their exposed cut sides will begin to sizzle softly, releasing a fragrant, fruity steam. The little pops and sizzles indicate the start of caramelization, which deepens the tomato flavor. Distributing oil and seasoning now encourages even blistering. Common mistake to avoid, overcrowding the dish can trap steam and prevent browning, so spread tomatoes out in a single layer.
Bake for 15-20 minutes, until tomatoes are "burst" and slightly blistered on the outside.: You will notice the skins wrinkle and split, and pockets of syrupy juice will appear at the cuts, giving off a sweet roasted aroma. That visual gloss and the faint scent of caramelized tomato signal readiness. If you rely solely on time, you may miss the moment; instead, watch for those visual cues. An error people make is leaving them in too long, which can dry them out, so remove when they look glossy and slightly collapsed.
Meanwhile, in a medium mixing bowl, toss trimmed asparagus with remaining olive oil, salt & pepper.: When you toss the asparagus, feel for even coating and listen for a light clink as the spears move together. The oil ensures a golden surface during the final roast, and seasoning now builds layers of flavor. Coating unevenly will create hot spots where some spears overbrown while others remain underdone, so take a moment to distribute oil thoroughly.
Once tomatoes are blistered, add prepared asparagus to baking dish. Drizzle with balsamic vinegar and toss with tomatoes.: As you combine the vegetables, the hot tomatoes will release fragrant steam that blends with the balsamic's sweet acidity. The tossing action helps the asparagus pick up the sticky, savory-sweet juices, which both flavors and slightly softens the spears. If you add the asparagus too early, it can overcook and become limp, so timing here is key. Use tongs or a spatula to gently turn everything so the glossy balsamic coats evenly.
Bake another 5 minutes. Asparagus should be tender-crisp.: During this short roast you will hear a gentle sizzle as the asparagus finishes cooking, and the color will deepen to a vibrant green with slight blistering at the tips. The goal is tender crisp, where a bite yields a pleasant snap and tender interior. Overbaking will cause limp, stringy stalks, so check at four minutes if your asparagus is thin. If it needs more time, add one minute increments to avoid overshooting the perfect texture.