Cook diced bacon in a skillet over medium heat until crispy; remove and set aside, keeping the bacon fat in the pan. Sauté chopped onion in bacon fat until translucent, about 4-5 minutes.

Add diced Gala apples and minced garlic; cook for an additional 3-4 minutes. Stir in fresh herbs, brown sugar, smoked paprika, and garlic powder. Cool slightly and mix in reserved bacon.

Take the beef tenderloin, trim any excess fat, and slice it lengthwise to create a hinge. Pound to an even 1-inch thickness.

Spread stuffing mixture evenly over the tenderloin. Roll tightly and secure with kitchen twine. Rub with olive oil and season with salt and black pepper.

Preheat oven to 400°F. Sear rolled tenderloin in olive oil for 3-4 minutes on each side until browned. Transfer skillet to oven and roast for 20-25 minutes, until thermometer reads 125-140°F.

Remove skillet and tent tenderloin with foil; rest for 10-15 minutes to redistribute juices.

De-glaze skillet with beef broth, add apple bourbon extract, Worcestershire sauce, and Dijon mustard. Simmer for 5 minutes.

Mix cornstarch with water and stir into the gravy; thicken to desired consistency. Finish with unsalted butter.

Slice tenderloin into medallions, drizzle with gravy, and serve alongside favorite sides.