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This impressive stuffed flank steak is filled with tangy cranberries, creamy cheeses, and herbs—rolled, seared, and baked into a savory holiday-worthy main dish.
For the Marinated Steak:
4 pounds flank steak
1 teaspoon sea salt
1 cup cranberry jelly
1/4 cup balsamic vinegar
2 sprigs rosemary
1 white onion, sliced
1 tablespoon garlic, minced
1/2 to 1 tablespoon peppercorns, freshly cracked
1 cup blue cheese (for rolling)
For the Cranberry Filling:
1/2 cup cranberries
1 tablespoon fresh rosemary
1 small shallot
1/4 cup chopped walnuts
1 cup blue cheese, crumbled
4 oz cream cheese, room temperature
1 teaspoon black pepper
Marinate the Steak
Place flank steak in a Ziplock bag with cranberry jelly, balsamic vinegar, rosemary sprigs, onion slices, and minced garlic.
Seal and marinate for at least 3 hours (up to 8 hours).
Remove from marinade, pat dry, season with sea salt and bring to room temperature.
Make the Filling
In a food processor, combine cranberries, rosemary, shallot, walnuts, blue cheese, cream cheese, and black pepper.
Pulse for about 30 seconds until just combined but still textured.
Assemble the Steak
Butterfly the steak (slice horizontally, but not all the way through). Pound gently to even thickness.
Spread the filling evenly over the steak.
Roll up the steak tightly and tie with kitchen twine. Wrap in plastic wrap and chill for 10–15 minutes.
Cook the Steak
Preheat oven to 350°F (175°C).
Heat an oven-proof skillet (cast iron preferred) over medium-high heat.
Roll steak in cracked pepper to coat the exterior.
Sear steak for 2 minutes on each side.
Transfer skillet to oven and bake for 20 minutes for medium-rare (or until internal temp reaches 130–135°F).
Rest and Serve
Remove steak from oven and let rest for 10 minutes.
Slice into pinwheels and serve warm.
Trim excess fat before rolling to keep the log tight.
Ask your butcher to butterfly the steak for you to save time.
Marinate for a minimum of 3 hours for best flavor.
Chill before searing for easier handling and better shape retention.
Use a meat thermometer to avoid overcooking.