Juicy Pineapple Heaven Cake

Packed with cheesy goodness, fresh spinach, a kick of garlic, and sweet bites of sun-dried tomatoes, these thinly cut, marinated flank steak rolls are seriously eye-catching and full of flavor. No fancy steakhouse needed—they're sure to wow folks whether you're celebrating or just hanging at home on a Saturday. Slice in, and you'll see awesome swirl layers of melty cheese and bold Mediterranean notes alongside juicy beef every single time.

Unbeatable Appeal

• With tender beef rolled up and gooey cheese tucked inside, these pinwheels instantly turn plain flank steak into a total showoff—you'll surprise everyone with how cool they look
• That cheesy, beefy combo punches up the savory, meaty flavor that real steak fans can't get enough of
• Serve 'em sliced thick for a main dish or thin for party snacks—they work both ways, super flexible for any occasion
• Prep ahead and keep chilled till you need 'em, giving you more chill time (and less stress) when company comes by

The very first time I whipped up these steak rolls was for my husband’s birthday after spotting something similar at a fancy restaurant. When I set the platter down, his jaw hit the floor! Dad-in-law, who's usually quiet at dinner, wouldn't stop talking about them—totally hooked. Now, we make 'em for every big family get-together, and it's a go-to happy dish in our house.

Top Ingredients

• Flank steak: keeps things juicy and packed with taste, especially if you get one with a solid thickness and nice little streaks of fat
• Olive oil: is what starts your marinade right—it softens up the meat and adds a smooth, lush flavor (grab extra virgin for the most taste)
• Soy sauce: dials up savory flavor and helps turn a tough cut tender—pick low-salt if you like to tweak the saltiness
• Red wine: gives the meat a little tang and some deep flavor—no need to splurge, just use one you'd drink
• Worcestershire sauce: brings a zippy, almost sweet punch thanks to its secret blend; even a splash totally changes the marinade
• Dijon mustard: has a nice sharpness and helps everything in the marinade stick well to your steak
• Swiss cheese: gets nice and melty, popping with nutty goodness against the meat (Gruyère’s also great here)
• Spinach: gives a shot of green color and freshness, taking the edge off all the hearty stuff and sneaking in some vitamins
• Sun-dried tomatoes: toss in sweet-tart bites through every swirl—oil-packed ones blend in the best

Easy Creation Process

Resting the Steak:

Once the steak's cooked, pull it from the oven, drape foil over it (not too snug), and let it hang out for 10 minutes. That way, the tasty juices settle in and don't leak all over when you slice. Yank any string or toothpicks before cutting and grab a sharp knife—slice the roll into thick rounds to show off the swirled middle.

In the Oven:

Slide your rolled steak into the preheated oven, no cover. Bake it 60–70 minutes if you like it mostly pink in the middle. It's always smart to poke a thermometer into the thickest chunk—145°F is pink and juicy, 160°F is less pink and more firm. The outside will go golden and caramelized as it bakes.

Rolling It Up:

Set the steak so a short edge faces you. Roll super snug from that edge, jelly-roll style, gently squishing any filling back inside if it tries to escape. Tie it up tight every inch or so with string or use soaked toothpicks so they don’t burn. Flip the seam down in your greased dish so it stays wrapped.

Layering Everything:

Sprinkle on three tablespoons of seasoned breadcrumbs and two tablespoons of minced onion, lightly pressing so they stick to the garlicky base. Lay down two cups of spinach leaves—overlap 'em to make a blanket. Next, toss on a cup shredded Swiss cheese and a quarter cup of shredded Parmesan, mixing them a little right on the steak with your hands. Last, scatter a half cup of drained, chopped sun-dried tomatoes all over.

Flavor Paste:

Smash up four minced garlic cloves with half a teaspoon of salt using the flat part of your knife until it gets pasty. This smooth paste spreads way easier and keeps the garlic taste mellow. Rub it all over the steak, right to the edges, for top-to-bottom flavor.

Getting Ready to Bake:

Once your steak's soaked up all the marinade, pull it from the fridge at least half an hour before baking to knock off the chill. Heat your oven to 350°F and grease a roasting pan good and proper. Take the steak out of the marinade (toss that liquid), then get it bone-dry with paper towels so it browns instead of steams.

Marinating Time:

Pop your prepped steak into a big zipper bag or flat dish and pour on that marinade. For bags, squeeze out the air before sealing so everything coats well. Stick in the fridge for at least 8 hours (overnight’s best), flipping it once if you remember. The steak gets tender and deep-flavored thanks to the marinade soaking right in.

Pounding the Meat:

Set your steak between sheets of plastic wrap and pound it out to about half an inch all around—center out—using a meat mallet or a heavy pan. Doing that helps tenderize it too. Grab a sharp knife and make shallow criss-cross marks about an inch apart on one side, like a diamond pattern, but don't cut all the way through.

Mixing the Marinade:

Throw a quarter cup olive oil, three tablespoons soy sauce, two tablespoons red wine, one tablespoon Worcestershire sauce, two teaspoons Dijon mustard, a tablespoon lemon juice, three minced garlic cloves, one teaspoon Italian seasoning, and half a teaspoon pepper in a bowl. Whisk like crazy till it all comes together and looks smooth—this kicks off the steak’s flavor journey.

Key Pointers

• Scoring the steak (little shallow cuts) helps the marinade soak in deeper and makes rolling it way simpler
• Letting the meat lose its chill on the counter before going in the oven helps everything cook nice and even
• Dry steak after the marinade is a must for a killer brown crust and max flavor
• Twine beats toothpicks for holding the roll since you get even pressure and it stays tight
• Letting your roll rest before slicing keeps the juices locked in so every slice is moist and tasty

Pin it

After making these for the first time, I figured out a quick swipe of olive oil outside the rolled steak makes the crust even more amazing and golden. My usually picky daughter surprised us all—she came back for seconds and now begs for them every birthday. When that cheese melts inside the steak, those rich, creamy pockets just take every bite up a notch.

Picture-Perfect Plating

Place the pinwheels on a bed of mashed potatoes—great for catching tasty drippings and making the whole meal pop. The cool swirl design always has folks talking. For fancier nights, I like pairing with roasted asparagus and a drizzle of balsamic reduction (looks and tastes fancy). Or, slice thinner and serve over soft polenta for appetizer bites people can't stop grabbing.

Fun Switch-Ups

Want a Greek-style twist? Use feta, swap spinach for basil, and toss in Kalamata olives. For some Southwestern flair, try pepper jack, roasted poblanos, and a sprinkle of taco spice in place of Italian seasoning. Craving classic steakhouse vibes? Shake things up with blue cheese, crisp bacon, and some sautéed mushrooms inside. Or go breakfast-style—stuff with scrambled eggs, shredded cheddar, and hash browns for a morning wow-factor.

Simple Storage

Stick leftover wheels in a tightly sealed container and get them in the fridge within two hours so they stay fresh. They'll taste great for about three days. To warm them up, set your oven to 300°F, put pinwheels on a tray, cover with foil, and heat for 15–20 minutes till they hit 165°F in the middle. Microwaving makes them rubbery—skip it! Want to prep ahead? Roll them up, keep in the fridge all wrapped up, and bake within 24 hours when you're ready.

Pro Tips

• Soak your butcher’s string in water for five minutes before tying to keep it from burning
• Even out thicker steak spots before marinating so your roll cooks perfectly all over
• Sear the rolled steak in a hot skillet before baking for even more rich, caramelized flavor
• For sharp pinwheel slices, let the cooked roll cool for 20 minutes, then chill it another 30 in the fridge before cutting with your sharpest knife
• Add a splash of red wine to the pan after baking, scrape up the bits, and whisk in a spoonful of butter for an easy, silky sauce

Pin it

What started as me trying out a steakhouse idea at home has turned into something we pull out for every celebration. Rolling and stuffing a basic cut of flank steak feels kind of magical—you end up with something that looks fancy, but is totally within reach. The combo of soft, melty filling and juicy meat always wins everyone over, whether it's for special guests or a cozy family dinner. It's that sweet spot where cooking feels both easy and fancy at the same time, making it super satisfying every single time.

Frequently Asked Questions

→ Is it okay to swap in fresh pineapple for canned?

Yep, you sure can. Cut up and blend your fresh pineapple to crush it, then get out as much extra juice as possible using a mesh strainer or by pressing with your hands. Just be aware that fresh fruit is usually juicier!

→ What's the easiest way to tell if my cake's baked all the way?

Poke the middle with a toothpick or thin knife. If it comes out clean or has a few crumbs (but isn't gooey), you're good to go. The top should look nicely browned and bounce back if you press it lightly.

→ Do I need to make it right before serving or can I prepare ahead?

You can totally prep this one early. It actually gets tastier when it sits overnight. Keep it tightly wrapped at room temperature for a few days, or chill in the fridge if you want it to last longer.

→ Will the cake hold up if I freeze it?

This cake freezes like a dream. Wrap it first with plastic and then with foil. It lasts in the freezer up to three months. Thaw overnight in the fridge or leave out for a few hours. Wait to add any glaze until it's thawed.

→ Stuck without sour cream—what else can I use?

You can use Greek yogurt without any fuss. It'll taste just as good and still keep the cake soft and tangy. Buttermilk works in a pinch, but it's a bit thinner so you might want to use a little less.