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Preheat the Oven: Preheat your oven to 400°F (204°C).
Prepare Herb Butter: In a small bowl, mix together the softened butter, thyme, rosemary, garlic, and a pinch of salt and pepper. Set aside.
Season the Steaks: Use half a Tablespoon of the steak seasoning for each steak. Season all sides of the steaks, gently pressing down to adhere the seasoning to the meat.
Wrap with Bacon: Wrap a slice of bacon around the sides of each steak. Secure the bacon where the ends meet with a toothpick.
Sear the Steaks: Heat a large cast iron or ovenproof skillet over medium-high heat. Once hot, add the olive oil and swirl to coat the bottom of the pan. Place the steaks in the skillet. Sear the first side for about 1-2 minutes until a golden-brown crust forms. Flip the steaks over and sear the second side for another 1-2 minutes.
Sear the Bacon Edges: Remove one steak to a clean plate. Use tongs to carefully hold the other steak on its side to sear the bacon-wrapped edges. Rotate the steak to ensure all bacon edges are seared, about 30 seconds to 1 minute per side. Repeat with the remaining steak.
Bake the Steaks: Return both steaks to the skillet. Insert an oven-safe meat thermometer into the thickest part of one steak. Transfer the skillet to the preheated oven. Bake for approximately 8-12 minutes or until the internal temperature reaches 130°F (54°C) for medium-rare doneness. Remember, the internal temperature will rise about 5°F (3°C) due to carryover cooking.
Rest and Serve: Once the desired doneness is reached, remove the steaks from the oven. Transfer them to a cutting board and top each steak with a dollop of the prepared herb garlic butter. Tent lightly with aluminum foil and let them rest for 5 minutes to allow the juices to redistribute throughout the steak.
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