The first time that I ever made this, was about 10 years ago! It was so good, so delicious, and SO easy, that I can’t even count how many times that I’ve made it since then! The recipe is VERY loosely based on an old Sandra Lee Semi-Homemade recipe from the Food Network channel, but I’ve tweaked it over the years to use a few more ingredients, as well as kick the flavors up a bit adding a marinade! I do still use a (decent) boxed stuffing, but you can certainly make that homemade as well. But during the summer, when I have an abundance of tomatoes, the ease of this “Steak Pinwwheels with Oven Roasted Tomato & Artichoke Stuffing” recipe really impresses every time!

You simply start by mixing up a very simple marinade in a large ziploc, add the flank steak, close it up well removing the air from the bag, and marinate it for several hours to overnight.

Next are the tomatoes. This part is up to you. Oh sure, you can cheat and use jarred, chopped, sun-dried tomatoes, but hey, it’s summer! Fresh produce is abundant and so much healthier! I LOVE to oven-roast tomatoes. It’s so easy to do it’s ridiculous. Then I just freeze them, and they’re right at hand for whenever I want them! So, I highly recommend that you whip up a nice big baking sheet of them, and then you’ll have them, too, at a fraction of the cost of one of those itty bitty “sun-dried” jars. (Do they even really actually dry them in the sun??) 😉 (*Another example of my oven roasted tomatoes here.)

To the finish line we go! Make the simple easy stuffing, adding the tomatoes and artichokes along with the stuffing mix once the beef broth and butter has come to a boil. Set it aside and fluff in 5 minutes, just as you normally would. Cover and let cool down. This part can even be done the day before. 😉

Lastly, you just remove the marinated flak steak from the marinade, letting the excess drip away, and place it onto a cutting board longways, making sure that the GRAIN is running lengthwise! VERY important. Cover the top of the steak with the stuffing. Then rollup, from long end/grain running longways, and secure the seam closed WELL with toothpicks.

Place seam side-down onto foil-lined and sprayed baking sheet and bake in a preheated oven for 40 minutes! Let rest, and slice against the grain for GORGEOUS, medium-rare pinwheels that are so tender and juicy that they almost melt in your mouth! *If you roast this longer, I cannot guarantee it’s tenderness. Flank steak should always remain pink to red inside for dishes such as this.

A seriously good, yet easy, company-worthy recipe!! In the summertime, we enjoy a simple garden salad and a hunk of crusty bread ‘n butter with this. But you can serve this with any side that you normally would enjoy with a good steak, too!

I hope that you enjoy as much as we do!

Steak Pinwheels with Oven Roasted Tomato Stuffing

Ingredients

1 (14 oz.) can beef broth
1/4 cup (4 Tbl.) real butter
1 (6 1/2 oz.) package beef flavored seasoned stuffing mix*
3/4 cup oven-roasted grape tomatoes, measure after roasting
1 (14 oz.) can quartered artichoke hearts in brine, drained and halved crossways
1 (1 1/4 lb.) flank steak

For Oven-Roasted Tomatoes:

grape tomatoes sliced in half lengthwise
EVOO or butter-flavored no-stick spray
pinch each salt, coarse ground black pepper, dried thyme

Steak Marinade:

1/2 cup soy sauce
1 Tbl. worcestershire sauce
1 large clove garlic, finely minced
1/4 tsp. onion powder
1/2 tsp. coarse ground black pepper

Instructions

In large ziploc baggie, add marinade ingredients. Add steak and turn to coat. Close bag well, removing the air. Marinate for several hours or overnight, turning now and then.

Put broth and butter into saucepan and bring to a boil over medium-high heat, stir in stuffing mix (*I only use Betty Crocker's Homestyle Beef Stuffing anymore), tomatoes and artichoke hearts. Cover saucepan and remove from heat. Let stand 5 minutes. Fluff stuffing lightly with a fork. Set stuffing aside to cool completely.

Heat oven to 425º F.

Lay steak flat onto cutting board, leaving excess marinade behind. (Discard marinade left in baggie). Cover evenly with stuffing. Roll up steak lengthwise (grain running lengthwise as well) to create a pinwheel effect, enclosing stuffing completely. Skewer seam WELL with toothpicks. Place steak roll seam side-down, onto foil-lined and sprayed baking sheet. Sprinkle top with a little coarse ground black pepper if you'd like.

Pop into preheated oven and roast until steak is browned and cooked through, for 40 minutes to be medium-rare inside. *This is exactly what you want so that it is juicy and tender, and not at all dry or tough!

Let rest 5 minutes before slicing against the grain into pinwheels.

To Oven Roast Tomatoes:

Preheat oven to 300º F. Line a baking sheet with parchment paper.

Slice grape tomatoes in half lengthwise and place onto prepared baking sheet with tomatoes facing cut side-up. Spray all with butter-flavored cooking spray or drizzle with EVOO, (just the top sides is all it needs). Sprinkle tops evenly with 1/2 tsp. kosher salt, 1/4 - 1/2 tsp.pepper (to taste), and 1/4 tsp. dried thyme crushed with your fingers when sprinkling. Pop into oven and bake for about 2 hours. (*You can also hurry the process using a higher temperature and less time).