Season the beef chuck cubes with salt and black pepper, then toss with the all-purpose flour to coat. Brown the beef in batches in the olive oil in a Dutch oven until deeply browned on all sides, adding more oil as needed if the pan gets dry.

Cook the diced onion in the browned drippings for 5 minutes, stirring, until softened. Add the minced garlic and tomato paste and cook for 1 minute until fragrant.

Pour in the apple cider and scrape the bottom of the Dutch oven to release browned bits. Add the beef broth, maple syrup, chopped fresh sage, fresh thyme leaves, and the browned beef.

Bring the stew to a gentle simmer, then cover and simmer for 1 3/4 hours, keeping the surface bubbling steadily. Skim foam if it appears and stir once midway for even thickening.

Uncover and add the cubed butternut squash, sliced parsnips, and sliced carrots. Simmer for 45 minutes, stirring occasionally, until the vegetables are tender when pierced.

Stir in the dried cranberries and simmer for the last 10 minutes so they soften but still hold their shape. Serve hot, spooning the thickened maple-touched gravy over the beef and vegetables.