Get out and measure all of your ingredients.
Preheat the oven to 400 degrees and prepare a rimmed baking sheet with foil and a rack coated in cooking spray. Set aside.
Wash, trim and pat dry the asparagus.
Divide asparagus into piles of 3 to 5 stalks each. The size of your piles will depending on the thickness of your asparagus spears.
Make sure asparagus tips are covered with small pieces of tinfoil if desired. The tinfoil protects the asparagus tips from being burnt while baking. My husband never covers the tips and I always do. The choice is yours. If your tips darken too much for your liking while cooking take a moment to carefully wrap hot ends.
Sometimes I rub a little brown sugar into the bacon slices before wrapping them around each asparagus spear. Make sure the brown sugar side is touching your asparagus and is tightly wrapped. This extra step occasionally is a nice change.
Tightly wrap the bacon tightly around the asparagus, overlapping slightly, starting at one end finishing almost at the other, and place on the rack. Secure with a toothpick if necessary.
Mix the olive oil with the salt and pepper in a small bowl.
Brush over the asparagus and bacon.
Place the asparagus bundles on the prepared baking sheet.
Turn oven on to 400 degrees. The bacon wrapped asparagus should be in the oven while it preheats.
Bake with the oven rack on the upper middle position. Cook for 20 to 25 minutes or until the bacon is crisp and asparagus is tender.
Serve with sliced lemons and herbs, if desired.
Turn your oven up to broil, if desired, to crisp bacon further for about another 2 minutes at the end. Make sure asparagus tips are covered with tinfoil or watch closely so the tips don't darken too much if you decide to broil.