Preheat your oven to 325 degrees F. This is crucial to ensure that the roast cooks evenly. A well-heated oven will help develop a nice crust on the outside of the chuck roast.
Place a large Dutch oven over medium-high heat and add the vegetable oil. Allow it to heat until shimmering; this indicates it’s ready for the roast. A hot pot will give you that beautiful brown sear.
Season the beef chuck roast generously with Kosher salt and ground black pepper on both sides. This not only flavors the meat but helps to form that delicious crust.
Brown the roast on both sides for about 6 to 8 minutes. You want to see a nice, golden-brown color on the surface; this is where the flavor develops.
Once browned, carefully remove the meat from the pot and set it aside on a plate. This resting will help the juices redistribute, keeping the roast moist.
Add the diced yellow onion and red onion to the pot. Sauté them until translucent and lightly browned, which should take about 3 to 4 minutes. This step builds a flavorful base.
Stir in the minced garlic and pumpkin cubes, sautéing for an additional minute, until fragrant. The pumpkin will begin to soften, absorbing all those wonderful flavors.
Now it’s time to add the rest of the ingredients to the pot. Pour in the Worcestershire sauce, canned diced pineapple with juice, cinnamon, and nutmeg. Stir well to combine.
Return the browned beef to the pot, nestling it among the vegetables. Add the bay leaves, whole garlic cloves, and quartered red onion for additional flavor.
Cover the pot and place it in the preheated oven. Let it cook for 3 to 4 hours, or until it becomes fork-tender. The longer it cooks, the more tender and flavorful it will be.
After cooking, carefully remove the pot from the oven. Discard the bay leaves and serve the beef shredded, garnished with chopped cilantro and accompanied by lime wedges. This brightens the dish and adds a delightful tang.
