Season the cubed beef with salt and black pepper, then toss with the all-purpose flour until coated (about the look of a light dry powder layer). Heat olive oil in a Dutch oven over medium-high heat until shimmering, then brown the beef in batches so it sears instead of steams (about 2–4 minutes per batch) and transfer to a plate with a visible caramelized crust.

Cook the diced onion for 5 minutes until softened and lightly translucent, scraping up browned bits from the bottom as needed. Add the minced garlic and tomato paste and cook for 1 minute until fragrant and darker in color.

Pour in the apple cider and scrape the bottom of the pot to release any stuck fond, then simmer briefly to reduce (about 2–3 minutes).

Add the beef broth, maple syrup, chopped sage, thyme leaves, and the browned beef, then bring to a simmer and ensure the beef is mostly covered by liquid. Cover and simmer for 1 3/4 hours (105 minutes), checking for a steady gentle bubble with occasional stirring at least once so the gravy thickens.

Add the butternut squash, sliced parsnips, and sliced carrots, then return to a simmer. Simmer for 45 minutes until the vegetables are tender enough to pierce easily, with the surface gently bubbling and the gravy looking thicker.

Stir in the dried cranberries and simmer for the last 10 minutes so they plump and stay suspended in the sauce (look for bursts of color throughout). Serve hot, with extra chopped sage visible on top for a fresh herby cue.