Cheesy Pineapple Flank Steak Pinwheels

Cheesy Pineapple Flank Steak Pinwheels

Hot and fresh off the grill these cheesy pineapple flank steak pinwheels are filled with molten cheese and have a perfectly sweet and spicy flavor profile! I love coming up with new fun things to throw on the grill and these flank steak roll ups really were worth the effort. I like when you can do all the prep work in the kitchen and then head out to the grill packing a ton of flavor!

The inspiration for this recipe

It’s been the most dreary spring here with just a few spots of occasional sun, but when that sun comes it’s a rush to take advantage of it. I actually grilled a version of this recipe in the rain that was a complete failure, but I returned to the grill a few days later with renewed confidence and the sun at my back. I have done a lot of pineapple and jalapeno recipes on the site over the years and that play of sweet and spicy is always a winning combo. The main trick to these is rolling them super tight and grilling to a perfect medium to prevent too much of the cheese filling from dripping out.

Make the filling

Cheddar, arugula, jalapenos, and a little cream cheese to help it stick.

the filling for the roll ups

Butterfly the flank steak

Slice your flank steak in half the thin way, keeping a little bit intact like a hinge. The hinge should go along the grain.

butterfly the flank steak

Build the cheesy pineapple flank steak pinwheels

Cheese mixture goes down. Then thin slices of pineapple. You need them as thin as possible for this! You can use a peeler if it helps. The cheesy jalapeno mixture goes so well with the pineapple in this flank steak pinwheel.

fill the flank steak with cheese and pineapple

Roll it up tight. Put a million skewers in and slice it into pinwheels. I am joking about a million skewers, but you need at least 3 per roll. Don’t be afraid to add more! Any insurance to help these stay together on the grill is good.

the pinwheels are made

Grill the cheesy flank steak pinwheels

Grill the flank steak pinwheels on a very high heat for about 6 minutes per side, browning it up nice and cooking the center to medium. The high heat will also help sear the cheese to prevent more from falling out. There is no doubt that there will be cheese leakage here, but we are trying to minimize it. Searing it will form a barrier that holds some cheese in.

Cheesy Pineapple Flank Steak Pinwheels on the grill

Serve the flank steak pinwheels

Allow to rest for 5 minutes before serving. This will let the cheese congeal a bit so that when you cut into it, the cheese stays where it is supposed to be.

Cheesy Pineapple Flank Steak Pinwheels

These were so good. The meat was perfectly tender with just enough chew and meaty flavor you expect from flank steak. The spicy jalapeno and sweet pineapple were balanced and the arugula added a nice earthy flavor to the flank steak pinwheels. And the cheese formed a perfect sauce to complement the steak.

Cheesy Pineapple Flank Steak Pinwheels

Twists on this recipe

For more tips and tricks on how to make good flank steak pinwheels, check out this recipe. You could add a ton of different things to this, whatever your favorite steak flavors are! Just don’t overfill and roll it up tight or everything will come leaking out on the grill.

If you are looking for more great flank steak recipes, check out my hummus pinwheels, these chimichurri crunchwraps, or this carne asada noodle bowl.

Cheesy Pineapple Flank Steak Pinwheels

Pineapple, cheddar cheese, arugula, and jalapeno, all rolled up into a tasty flank steak pinwheel and grilled until browned and delicious.
Prep Time15 minutes
Cook Time10 minutes
rest30 minutes
Total Time55 minutes
Course: Main Course
Cuisine: American
Keyword: grilled, stuffed
Servings: 4 people
Calories: 550kcal


  • 1.5 pound flank steak bigger is fine
  • 2 cups cheddar cheese
  • 2 tablespoons cream cheese
  • 2 jalapenos diced and most of the seeds removed
  • 2 handfuls arugula chopped small
  • 1/2 a pineapple cut into thin planks as thin as possible! You could use a peeler


  • butterfly the flank steak. Cut it the thin way to open it up like a book leaving a hinge along the grain on one side.
  • mix the cheeses with the jalapeno and arugula until combined.
  • spread the cheeses on the laid out flank steak. Spread it thin and discard any extra.
  • Top with a layer of the thin pineapple.
  • roll up very tight. The grain of the steak should be going along the roll in a straight line, not rolled up with the roll.
  • Place 3 skewers where each roll will be, and cut in between the skewers to form the pinwheels. Chill to firm for a half hour.
  • Grill on high heat for about 6 minutes per side to brown and cook to a medium doneness.


Calories: 550kcal | Carbohydrates: 17g | Protein: 51g | Fat: 30g | Saturated Fat: 16g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 8g | Cholesterol: 166mg | Sodium: 486mg | Potassium: 811mg | Fiber: 2g | Sugar: 12g | Vitamin A: 1042IU | Vitamin C: 64mg | Calcium: 474mg | Iron: 3mg


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