Pre-heat oven to 400ºF.
On a large baking sheet, with a wire rack placed on top, lay bacon.
Bake until bacon is cooked but still pliable, about 20 minutes.
Increase oven heat to 425°F.
Line a large sheet pan with parchment paper.
On a lightly floured surface, roll the puff pastry out to a large rectangle.
Square off edges and cut the rectangle into 8 even squares.
Toss asparagus in olive oil and season with salt and pepper.
Brush each square of puff pastry with egg wash.
Place a slice of cooked bacon on top, followed by 3 to 4 stalks of asparagus and a sprinkle of Parmesan.
Wrap bacon around asparagus and cheese, then wrap puff pastry around the bacon-asparagus bundle, overlapping the puff pastry ends to seal.
Brush each puff pastry with more egg wash.
Bake until puff pastry is golden and puffed, about 12 minutes.