Prep the meat by removing it from the refrigerator about 1 hour to 30 minutes before making. You can pound it out now between two pieces of parchment paper.
Preheat the oven to 425 degrees. Combined the dry rub mix ingredients and rub them on both sides of the flank steak. Place 3 pieces of cooking twine under the steak. Then set aside.
Prepare the stuffing mix by and then combine it all in a bowl. Mix well.
Add the stuffing mix to the flank steak in the middle, leaving about an inch from the edges. Then roll the steak like a taco with the grain. try to touch the ends on top and secure it all with the twine.
Brush the cast iron pan with 1 tbsp of the extra virgin olive oil and then place the rolled steak in the pan. Drizzle on another tablespoon and then place in the oven for 25 minutes.
While the flank steak cooks, toss the asparagus with the last tablespoon of extra virgin olive oil.
When the time is up remove the flank steak from the oven, add the asparagus and turn the oven to broil. Sprinkle a little extra salt on the asparagus and then put the pan back in the oven for 10 minutes.
When time is up, remove it from the oven and check the doneness with a meat thermometer. The Italian Stuffed Flank Steak should be covered with foil and rest 10 minutes and the temperature of the meat will continue to rise. Medium is 130 degrees. Rested it will be between 137- 140
Once the meat had rested, slice and serve it with the asparagus and any pan drippings.