After the silver skin is removed, slice tenderloin in the middle, lengthwise, making sure to not go all the way through. Make a few slits on each side so the meat sits flatter on the cutting board.
Place plastic wrap on top and evenly pound the meat down to about ¼-inch thick.
Brush on pomegranate molasses before placing prosciutto, enough to cover the meat, leaving an inch around the edges. Preheat oven to 375ºF.
Spoon the stuffing on top, leaving 2-inches around the edges. Add shredded cheese and sprinkle on hot paprika.
Roll up the meat tightly and, using kitchen twine, tie a knot at one end, leaving a 2-inch-long string for later.
Go round and round to the other end, crisscrossing the twine and going back to the starting point. Tie a knot with the 2-inch string and cut off the extra twine. Secure the ends with toothpicks.
Generously season the stuffed tenderloin with salt and pepper.
In an oven-proof skillet over medium-high heat, add oil and when it starts shimmering, add prepared tenderloin, seam, side down, and sear until brown, about 2 minutes. Flip it over and transfer to the preheated oven. Cook for 18 to 22 minutes or until the internal temperature reaches between 140ºF to 145ºF.
Remove from the heat and transfer meat to a cutting board, cover loosely with foil and allow to rest for 10 to 15 minutes while making the pan sauce.