Tender, juicy grassfed flank steak stuffed with cream cheese, Monterey Jack, Jalapeños, garlic, parsley, basil, and chives – rolled up and baked to perfection for a delicious and impressive dinner. A creative way to mix things up with your next 1915 Farm flank steak!
Bring cream cheese to room temperature.
Thinly slice the jalapeños and remove seeds and ribs. Heat a skillet over medium heat, add olive oil, and sauté jalapeños until tender.
Combine garlic, parsley, basil, chive, olive oil, salt, and pepper in a small bowl. Add cooked jalapeños and combine. Then add cream cheese and Monterey Jack to herb mixture.
Slice steak horizontally to butterfly it and pound into 2 thin rectangles. Position steak so that the grain runs parallel to the edge of the counter and spread herb mixture evenly over surface of steak. Leave a 1-inch border along the top edge.
Starting from the bottom edge and rolling away from you, towards the top, roll steak into tight log and place on cutting board seam-side down.
Starting in the middle of the steak roll, tie a piece of kitchen twine to secure the steak. Working outward from the center, tie additional kitchen twine, in one inch intervals, until the whole steak roll is tied up.
Using a sharp knife, slice roll between pieces of twine into 1-inch-thick pinwheels. Season pinwheels lightly with salt and black pepper.
Skewer each pinwheel with a toothpick.
Preheat oven to 350°
Heat a cast iron skillet over medium high heat. Place pinwheels in pan and brown for 3 minutes or so. Flip over and brown on the other side for 2 minutes.
Transfer skillet into preheated oven and cook for about 8-10 minutes or until steak reaches desired doneness.
Remove from oven, tent with foil and let rest for 5 minutes.
Remove twine and toothpicks and enjoy!