Meanwhile, wash and pat 1 lb. asparagus spears dry with paper towels, then trim off any woody stems at the bottom. Separate the asparagus into four equal sized bunches.
Wrap each bundle with one of the 4 slices sugar-free bacon, overlapping the bacon as little as possible. This will prevent undercooked parts of the bacon and allow as much fat to render as possible. Use a toothpick if necessary on the underside of each bunch to help hold the bacon together.
Lay each bundle on a slotted pan or use a cooling rack on top of a parchment-lined baking sheet (this will allow the fat to drip away from the bacon as it renders).
Drizzle or spray with 1 tablespoon olive oil and sprinkle ⅛ teaspoon pepper on top. Bake for 10 minutes, then flip the bundles and bake another 8-10 minutes, or until the bacon is crispy and the asparagus is tender.
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Notes
For extra flavor, drizzle 1 tablespoon maple syrup or 1 tablespoon balsamic reduction over the plated bundles, or sprinkle with 2 tablespoons crumbled goat cheese.Refrigerate cooled leftovers in an airtight container for about 2 days, or freeze for up to 3 months. Thaw and reheat in the oven.If your bacon slices are especially thin, you may find it easier to wrap them if you first cut them in half horizontally.