Combine pineapple juice, soy sauce, canola oil, garlic, pepper and brown sugar and stir until brown sugar is dissolved. Pour into a zippered plastic bag.
Add the flank steak to the bag, zipper it up, squish it around and then let it marinate in the fridge for at least 4 hours.
When you are ready to cook, prep your pineapple! Cut off the base and the top, then stand it up and slice off the peel, making sure to get all those little prickly spots off. Now slice it into 1 to ½ inch round slices cutting out the middle core with a paring knife.
Heat the grill to high and grill the steak, about 5 minutes per side (and 135 on a meat thermometer) for medium rare. Cover it with foil while you cook the pineapple.
Place the pineapple on the grill for 2 to 3 minutes per side. I like to slide a spatula underneath before I turn them to make sure they come off without sticking.
Slice up the steak, cut the pineapple rounds in halves and serve it up!
Notes
Pineapple: I love slicing up a fresh pineapple, but if you aren’t up for that, you can use canned pineapple rings.
Steak: We love a flank steak for this recipe, but you can also use skirt steak, sirloin tip steak or hanger steak.
Soy Sauce: As always, we highly recommend using low sodium soy sauce. You can add salt but you can’t take it out!
Pineapple Juice: Look for this in the juice section of your supermarket. You’re going to have leftover juice, but you can use it to make Pineapple Shrimp Pasta!