Preheat oven to 425° and prepare a baking sheet with aluminum foil or parchment paper.
Spread the asparagus and tomatoes on the prepared baking sheet, then drizzle with olive oil. Season with salt and pepper. Bake 12-15 minutes, until tender.
Meanwhile, in a large saucepan, heat 2-3 inches of water to boiling. Break one egg into a small bowl. Slip the egg into boiling water, then reduce to a simmer. Cook 3-5 minutes, until egg white is completely set. Use a slotted spoon to remove the egg, then place on a paper towel-lined plate. Repeat with remaining eggs.
Serve eggs over roasted asparagus and tomatoes and season with additional pepper if desired.