Stuffed Flank Steak with Balsamic Glaze
Stuffed flank steak is probably the most flexible recipe I have right now, and it’s simple. The glaze is optional, but it’s delicious, I like to make it ahead of time so I can be attentive while it cooks down.
Servings Prep Time
8pinwheels 25min
Cook Time
15min total
Servings Prep Time
8pinwheels 25min
Cook Time
15min total
Stuffed Flank Stead
Balsamic Glaze (optional)
The filling
  1. In a skillet with a lid, heat the olive oil over medium heat. Add the mushrooms and saute until they are golden, about 5 minutes.
  2. Add the shallots and cook for an additional 2 min while string.
  3. Reduce the heat to low and add the spinach, a little more olive oil if you need to and the garlic salt. Stir to mix and put the lid on allowing the spinach to wilt. Pull this off the heat, stir in the sun dried tomatoes and move on to stuffing the steaks (see notes).
Steak Pinwheels
  1. Preheat the oven to 350C
  2. Place the steak on a cutting board with the grain of the meat parallel to the edge of the counter. Pound the meat thinner to make it easier to roll, or if it’s really thick/uneven butterfly it and then pound it flat.
  3. Starting with the edge closest to you begin to plop the filling on the meat. Evenly spread it out avoiding the top third of the steak.
  4. Starting with the edge closes to you roll the steak like a big meaty jelly roll.
  5. Secure with toothpicks and slice into 2 inch thick pinwheels.
  6. Heat an oven proof (I like cast iron for this) skillet over medium heat with a drizzle of olive oil.
  7. Lay the pinwheels cut side down and sprinkle with half the herb seasoning, then place them seasoning side down in the hot skillet. Sprinkle the rest of the seasoning over the pinwheels while they sear.
  8. Once they are nice and brown on the bottom (about 1 min) flip the pinwheels over and sear the other side for about two minutes.
  9. Sprinkle the Parmesan cheese over the steaks.
  10. Place them in the oven for 7-10 min until the desired doneness is reached. If the cheese hasn’t browned I like to give them a min under the broiler before I pull them out.
  11. Allow the steaks to rest for a few min before plating them and drizzling the glaze across the tops (if using it which you really should).
Balsamic Glaze
  1. While the pinwheels are in the oven and resting it’s time to make the glaze, if you are using it that is. In a small sauce pan mix the balsamic and brown sugar.
  2. Bring to a gentle simmer while stirring. Reduce the heat slightly and allow it to reduce by half. It’s really that simple. Drizzle over the finished pinwheels. Sometimes I make a double batch the day before and use it on other stuff too.
Recipe Notes

This can stand alone with a very simple side like rice to catch the extra juices.  Myself, I’m a veggie lover and so I make a simple side salad or steamed carrots.

Note about the balsamic vinegar, you don’t have to break the bank but do pick one that has a nice well rounded flavor.  In making the glaze those flavors will be concentrated and made a little sweet, so it’s best to start out with a decent quality vinegar.  

Note about the filling, this can be made up to two days ahead of time.  Just store in the fridge in a airtight container until you are ready to stuff the steak.  Any longer than two days and I find it loses it’s bright flavor and color.