Cut the beef chuck roast into 1-inch cubes, season generously with salt and pepper, and toss with a splash of olive oil to coat.

In a large Dutch oven, heat a drizzle of olive oil over medium-high heat. When shimmering, add the beef cubes in batches to avoid overcrowding. Sear until browned on all sides (about 5-7 minutes). Remove the beef and set it aside.

In the same pot, add more olive oil if needed, then toss in the red onion. Cook for about 5 minutes until softened, then add garlic and thyme; sauté for another minute until fragrant.

Stir in the tomato paste and cook for 1-2 minutes to deepen the color. Pour in the balsamic vinegar and maple syrup, allowing it to reduce for a minute.

Add the red wine or beef broth—scrape the bottom of the pot to release those flavorful bits. Let it simmer for about 3-4 minutes.

In a small bowl, whisk together the flour with 1/2 cup of cold water until smooth. Pour this mixture into the pot while stirring continuously to avoid lumps.

Add the beef back into the pot along with bay leaves and rosemary. Now pour in the beef broth, bring the stew to a gentle boil, then reduce to a simmer for about 1 hour, uncovered, stirring occasionally.

After an hour, add the butternut squash. Cover and continue to simmer for an additional 30 minutes until the squash and beef are fall-apart tender.

Remove the bay leaves and rosemary stems. Garnish with fresh parsley before serving.