Peel apple, quarter, and remove core. Cut into ¼" dice. Peel and halve shallot. Slice half into ¼" rounds and mince other half. Stem sage and slice thinly. Coarsely chop cranberries. Cut twine into four equal pieces. Place pork tenderloin on a separate cutting board and make a lengthwise cut through the center. Stop ¼" short of opposite edge of tenderloin so pork remains in one piece. Lay pork flat, cover with plastic wrap, and pound out to a ¼" thickness. Season both sides with ¼ tsp. salt and a pinch of pepper.

Toss butternut squash, shallot rounds, half the sage, 1 tsp. olive oil, and a pinch of salt and pepper together on prepared baking sheet. Spread into a single layer on one half of prepared baking sheet and roast until squash is tender, 14-16 minutes. While vegetables roast, place a large non-stick pan over medium heat. Add 1 tsp. olive oil, apple, and minced shallot to hot pan. Stir occasionally until shallot is translucent, 1-3 minutes. Add ¼ cup water, cranberries, and Dijon. Stir occasionally until apples slightly soften, 1-2 minutes. Transfer to a plate and let cool 3 minutes. Season with a pinch of salt and pepper. Wipe pan clean and reserve.

Place ½ cup filling (reserve remaining for sauce) down center of pork tenderloin and roll. Tie pork tenderloin closed with twine. Return pan used to cook filling to medium-high heat and add 1 tsp. olive oil. Add pork tenderloin to hot pan and sear on two sides until browned, 3-4 minutes per side. Remove pan from burner.

Add pork tenderloin to empty half of baking sheet. Roast until pork tenderloin reaches a minimum internal temperature of 145 degrees, 12-14 minutes. Rest 5 minutes, then slice into ½"-thick slices.

When pork has 5 minutes left to roast, return pan used to sear pork to medium heat. Add reserved filling, demi-glace, remaining sage, and ½ cup water to hot pan. Bring to a simmer and stir often until thickened enough to coat the back of a spoon, 3-5 minutes. Remove from burner. Plate dish as pictured on front of card. Bon appétit!