📖 Instructions

1. First, let's prep the pineapple BBQ sauce: In a medium saucepan, combine the crushed pineapple (with juice), ketchup, brown sugar, apple cider vinegar, soy sauce, Dijon mustard, Worcestershire sauce, garlic powder, onion powder, smoked paprika, black pepper, and a pinch of red pepper flakes. Stir it all together to ensure everything is well mixed.
2. Bring the sauce to a simmer over medium heat: Once simmering, reduce the heat to low and let it simmer for about 15-20 minutes, stirring occasionally. This allows the flavors to meld together and the sauce to thicken slightly. Keep an eye on it so it doesn't burn! You are looking for a nice, thick consistency.
3. While the sauce simmers, prepare the flank steak: Pat the flank steak dry with paper towels. This helps to get a good sear on the grill. Season it generously with salt and black pepper. Don't be shy with the seasoning—it really enhances the flavor of the steak. I like to use kosher salt for this.
4. Now, it's grilling time! Preheat your grill to medium-high heat: Make sure the grates are clean and lightly oiled to prevent the steak from sticking. Place the flank steak on the hot grill and sear for about 4-5 minutes per side for medium-rare, or longer if you prefer it more well-done. The internal temperature should reach 130-135°F for medium-rare. A meat thermometer is your best friend here!
5. During the last few minutes of grilling, brush the pineapple BBQ sauce over the steak: This creates a sticky, flavorful glaze. Be careful not to add the sauce too early, as the sugars in the sauce can burn. Apply a generous layer on both sides. I usually do this in the last 2-3 minutes of grilling.
6. Once the steak is grilled to your liking, remove it from the grill and let it rest for 10 minutes: This is crucial! Resting allows the juices to redistribute throughout the steak, resulting in a more tender and flavorful cut. Cover it loosely with foil while it rests. Don't skip this step; its important!
7. While the steak is resting, grill the pineapple chunks: Brush them lightly with olive oil and grill for 2-3 minutes per side, or until they have nice grill marks and are slightly caramelized. Grilling the pineapple brings out its sweetness and adds a delicious smoky flavor. A cast iron grill pan works well if you're looking to do it indoors.
8. Finally, slice the flank steak thinly against the grain: This makes it easier to chew and more tender. Serve the sliced steak with the grilled pineapple chunks and an extra drizzle of pineapple BBQ sauce. You can also garnish with fresh cilantro or parsley for a pop of color and freshness. I also love to serve mine with rice!