Preheat the oven: Preheat your oven to 375°F (190°C).
Prepare the pork: Remove any silver skin from the pork tenderloin. Place the tenderloin on a cutting board and butterfly it by making a lengthwise cut through the center, being careful not to cut all the way through.
Flatten the pork: Open the tenderloin like a book. Cover it with plastic wrap and gently pound the thicker sections until the pork is relatively even in thickness.
Season the pork: Season the inside with the kosher salt, black pepper, and garlic powder.
Prepare the apple: Core the apple and cut it into small pieces. Peeling is optional.
Make the filling: Combine the diced apple, shredded cheddar, Dijon mustard, and fresh thyme in a bowl. Stir in the optional pecans, cranberries, or sage if using.
Fill the pork: Spread the apple and cheddar mixture evenly over the flattened tenderloin, leaving a small border around the edges.
Roll the tenderloin: Starting from one long side, carefully roll the pork into a tight cylinder, keeping as much of the filling inside as possible.
Secure the pork: Tie the rolled tenderloin securely with kitchen twine at several intervals so it holds its shape during cooking.
Sear the pork: Heat the olive oil and butter in a large oven-safe skillet over medium-high heat. Place the stuffed tenderloin in the skillet and sear it on all sides until deeply golden brown.
Roast: Transfer the skillet to the preheated oven. Roast for approximately 20–25 minutes, but begin checking the internal temperature early because cooking time will vary according to the size and thickness of the tenderloin.
Check the temperature: Insert an instant-read thermometer into the thickest part of the pork. Remove it from the oven when it reaches at least 145°F (63°C).
Rest: Transfer the pork to a cutting board and allow it to rest for at least 3 minutes. A slightly longer rest can make slicing easier.
Slice and serve: Remove the kitchen twine and slice the tenderloin into thick medallions. Arrange the slices on a serving platter and spoon any pan juices over the top.