Preheat and prep. Heat your oven to 400°F (205°C).
Line a sheet pan with foil and place a wire rack on top. The rack helps the bacon crisp and keeps the chicken from sitting in rendered fat.
Mix the rub. In a small bowl, combine garlic powder, smoked paprika, onion powder, black pepper, salt, and optional cayenne. Stir in the chopped herbs if using.
Season the thighs. Pat the chicken very dry with paper towels.
Drizzle with oil and rub the seasoning all over, including the underside.
Wrap with bacon. For medium thighs, use one slice; for larger thighs, use two slices. Start at one end and wrap in a slight spiral so each turn overlaps. Tuck the end underneath.
If needed, secure with a toothpick placed horizontally so it doesn’t protrude upward.
Arrange on the rack. Place the wrapped thighs seam-side down on the rack with a bit of space between each piece for airflow.
Bake to crisp and juicy. Cook for 30–40 minutes, turning the pan halfway through. Start checking at 28 minutes. You’re looking for 165–175°F (74–79°C) in the thickest part.
Thighs do well on the higher end of that range for tenderness.
Optional broil. If the bacon isn’t crisp enough, broil on the top rack for 1–3 minutes, watching closely to prevent scorching.
Rest and serve. Let the chicken rest 5 minutes to reabsorb juices. Brush lightly with sugar-free BBQ sauce or a splash of hot sauce if you like. Serve with a simple side like roasted broccoli, a lemony salad, or cauliflower mash.