Trim the tough bottom 1-2 inches from each asparagus spear by snapping them at their natural breaking point or cutting with a knife. Rinse and pat the asparagus dry thoroughly—this is important so the seasoning adheres properly and they grill evenly without excess moisture. In a large bowl, toss the asparagus with the olive oil, salt, pepper, and garlic powder until every spear is evenly coated. Set aside while you prepare the bacon.
Divide the seasoned asparagus into 8 bundles of 3 spears each. Take one slice of bacon and wrap it around the middle of each bundle, tucking the ends under so they stay secure during grilling. I find that thick-cut bacon works best here because it's more forgiving and less likely to tear when wrapping. Arrange the wrapped bundles on a plate, ready to grill.
Preheat your grill to 400°F and lightly oil the grates to prevent sticking. Place the bacon-wrapped bundles directly on the grill, seam-side down first. Grill for 25-30 minutes, turning occasionally (every 8-10 minutes) to ensure the bacon renders and crisps on all sides while the asparagus becomes tender and lightly charred. The bacon will be the guide here—once it's golden and crispy, the asparagus underneath will be perfectly cooked.
Transfer the grilled asparagus bundles to a serving platter and let them rest for 2-3 minutes. This brief cooling allows the flavors to settle and makes them easier to handle without burning yourself. Serve warm as a side dish or appetizer.