Juicy Grilled Flank Steak Rolls

Okay, let’s be honest—regular steak is great and all, but have you ever rolled it up with a bunch of delicious stuff inside and turned it into the fanciest, most impressive thing you’ve ever grilled? Because that’s exactly what we’re doing here, and it’s about to change your entire grilling game.

These Juicy Grilled Flank Steak Rolls look like something you’d order at an upscale steakhouse for $45 a plate, but surprise—you’re making them at home in your backyard while wearing crocs and a questionable t-shirt. They’re juicy, flavorful, and stuffed with cheese, herbs, and whatever else your heart desires. Plus, they’re way easier to make than they look, which is basically the dream.

The flank steak gets pounded thin, loaded up with tasty fillings, rolled into perfect little bundles, and grilled to perfection. Every slice reveals a gorgeous spiral of meat and filling that’ll make you feel like a legitimate culinary genius. Whether you’re trying to impress dinner guests or just want to eat something that makes you feel fancy, these steak rolls are calling your name.

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Why This Recipe is Awesome

First things first: these things look absolutely spectacular. When you slice them open and see that perfect spiral of steak wrapped around melted cheese and herbs, you’ll want to take approximately 47 pictures before eating. They’re the definition of “wow factor” food.

But here’s the kicker—they’re not actually that hard to make. Yeah, there’s a little assembly involved, but it’s nothing crazy. You’re basically just pounding meat (great stress relief), adding toppings, rolling it up, and grilling. If you can make a burrito, you can make these steak rolls.

The flavor is next-level too. The marinade keeps everything juicy and adds tons of flavor, while the filling creates pockets of melted cheese and herbs in every bite. You get different textures and flavors in each slice, which keeps things interesting instead of just eating a plain piece of steak.

They’re also perfect for entertaining. You can prep these ahead of time, stick them in the fridge, and just throw them on the grill when your guests arrive. Suddenly you’re the person who “just whipped up some stuffed steak rolls” like it’s no big deal.

Ingredients You’ll Need

Here’s what you’re grabbing from the store—nothing too wild:

For the steak:

• 2 lbs flank steak (ask your butcher to butterfly it, or do it yourself)
• 3 tbsp olive oil
• 3 tbsp balsamic vinegar
• 3 cloves garlic, minced
• 2 tsp dried Italian seasoning
• 1 tsp paprika
• Salt and pepper to taste

For the filling:

• 1 cup fresh spinach leaves (packed)
• ½ cup sun-dried tomatoes (chopped, oil-packed work great)
• 1 cup mozzarella cheese, shredded (or provolone)
• ½ cup grated Parmesan cheese
• 4-6 slices prosciutto
• 2 cloves garlic, minced
• Fresh basil leaves (about ¼ cup)
• Salt and pepper to taste

For grilling:

• Kitchen twine or toothpicks (to secure the rolls)
• Olive oil for brushing

Optional garnish:

• Fresh parsley or basil
• Balsamic glaze for drizzling

Simple ingredients that pack a serious flavor punch.

Step-by-Step Instructions

1. Butterfly and pound the steak. If your butcher didn’t butterfly it, place the flank steak on a cutting board and carefully slice it horizontally (like opening a book), stopping about ½ inch from the edge. Open it up flat. Cover with plastic wrap and pound it to an even ½-inch thickness with a meat mallet. This ensures even cooking and makes rolling easier.

2. Make the marinade. In a bowl, whisk together olive oil, balsamic vinegar, garlic, Italian seasoning, paprika, salt, and pepper. Pour half over the pounded steak, spreading it evenly. Save the other half for later.

3. Layer the filling. Lay the spinach leaves over the steak, leaving about an inch border around the edges. Sprinkle with sun-dried tomatoes, mozzarella, Parmesan, minced garlic, and torn basil leaves. If using prosciutto, lay it over the cheese.

4. Roll it up. Starting from one long side, tightly roll the steak into a log, keeping the filling inside. Don’t stress if some filling escapes—just tuck it back in. The tighter you roll, the better it holds together.

5. Secure the roll. Tie kitchen twine around the roll at 1-2 inch intervals to keep everything together. Or use toothpicks every inch or so. Make sure it’s secure—you don’t want it unraveling on the grill.

6. Brush with remaining marinade. Coat the outside of the roll with the reserved marinade. This adds flavor and helps with browning. Let it sit at room temp for 20 minutes while you preheat the grill.

7. Preheat the grill. Get it to medium-high heat, around 400°F. Clean and oil those grates well—you don’t want your beautiful creation sticking.

8. Grill the roll. Place the steak roll on the grill, seam-side down first. Grill for about 4-5 minutes per side, rotating to get all sides evenly browned. Total cooking time is about 15-20 minutes for medium-rare (135°F internal temp).

9. Rest and slice. Remove from grill, tent with foil, and let rest for 10 minutes. This is crucial—don’t skip it. Remove the twine or toothpicks, then slice into 1-inch thick rounds. Arrange on a platter and prepare for compliments.

Common Mistakes to Avoid

Not pounding the steak evenly. If some parts are thick and others are thin, it’ll cook unevenly and be harder to roll. Take your time with the mallet and get it uniform.

Overfilling the roll. More is not always better here. Too much filling and it’ll burst out everywhere when you roll it. Keep it to a reasonable layer so everything stays put.

Rolling it too loosely. A loose roll means filling falls out and the whole thing can unravel during grilling. Roll it tight and secure it well with plenty of twine or toothpicks.

Not letting it rest before slicing. Cut into it immediately and all the juices (and possibly the filling) will run out. Give it 10 minutes to rest—use that time to make a side dish or just stand there admiring your work.

Forgetting to remove the twine before serving. Don’t be that person. Remove it right after resting, before you slice. Otherwise someone’s definitely getting twine in their mouth and that’s awkward for everyone.

Alternatives & Substitutions

Steak: Skirt steak works similarly to flank. You can also use a butterflied sirloin or even chicken breast if you’re not feeling beef. Just adjust cooking time accordingly.

Cheese: Fontina, gouda, or even feta work great. Blue cheese adds a fancy, sharp flavor if you’re into that. Mix and match based on what you like or what’s in your fridge.

Greens: Arugula, kale, or even roasted red peppers instead of spinach. IMO, arugula adds a nice peppery bite that works really well with the beef.

Meat additions: Italian sausage (removed from casing and crumbled) is amazing in the filling. Pepperoni works too if you’re going for pizza vibes.

Herbs: Fresh rosemary and thyme are great alternatives to basil. Chop them finely so they distribute evenly throughout the filling.

No grill? Sear the roll in a hot cast-iron skillet on all sides, then finish in a 375°F oven for 15-20 minutes until it reaches your desired doneness.

Final Thoughts

These juicy grilled flank steak rolls are the ultimate showstopper meal that’s surprisingly manageable to pull off. They look impressive, taste incredible, and make you feel like you actually know what you’re doing in the kitchen (even if you’re mostly winging it).

The combination of tender steak, melted cheese, and flavorful fillings creates something special in every bite. It’s restaurant-quality food without the restaurant prices or the need to change out of your grilling outfit.

Perfect for date nights, dinner parties, or just treating yourself because you’ve had a week and you deserve something fancy. The prep is totally doable, the grilling is straightforward, and the results are absolutely mouth-watering.

Now grab that flank steak and get rolling. Your inner chef is about to make an appearance!

FAQ (Frequently Asked Questions)

Can I make these ahead of time? Absolutely! Assemble the rolls completely, wrap them tightly in plastic wrap, and refrigerate for up to 24 hours before grilling. Just let them sit at room temperature for 30 minutes before hitting the grill. You can even freeze them (unbaked) for up to 2 months—just thaw in the fridge overnight before cooking.

What if I don’t have a meat mallet? Use a heavy pan, rolling pin, or even a wine bottle. Just cover the meat with plastic wrap first so you’re not cleaning meat bits off your makeshift mallet. The goal is even thickness, not necessarily a fancy tool.

How do I know when they’re done? Use a meat thermometer inserted into the thickest part (not the filling). You want 130-135°F for medium-rare, 135-145°F for medium. Remember it’ll continue cooking a bit while resting. If you don’t have a thermometer, the roll should feel firm but still have some give when you press it.

Help! My roll is falling apart on the grill! Make sure you tied it securely enough—use plenty of twine at close intervals (every 1-2 inches). Also, sear the seam side first to help seal it. If toothpicks aren’t holding, definitely switch to kitchen twine. And resist the urge to flip it too often—let each side develop a good crust before moving it.