Heat the oven to 425°F. Peel the squash in long downward strokes and halve it through the neck. Scoop out the seeds and cut 2.5 pounds into uneven 1-inch cubes. Whisk maple syrup, olive oil, apple cider vinegar, kosher salt, black pepper, cinnamon and thyme for 30 seconds. Then fold the cubes through the glaze for 60 seconds with broad scooping motions. The cubes should look glossy but not sit in a puddle. You'll smell cinnamon and thyme before the tray enters the oven. Take 10 to 12 minutes for this prep. Cut smaller than 1 inch and the edges dry before the centers soften. Cut larger and the maple darkens first. Uniform-enough cubes roast at the same pace.

Spread the coated cubes across a rimmed sheet pan so most pieces have bare metal around them. Roast at 425°F for 15 minutes. Then turn every cube with a thin spatula and shift the pale pieces toward the hotter outer edges. Keep the darker pieces closer to the center. (I tested 400°F first, the squash softened but never developed the same caramelized corners.) At minute 15, the undersides should show amber patches while the tops stay bright orange. You'll hear a soft sizzle when the pan leaves the oven. If syrup pools between crowded cubes, they'll steam and turn watery. Miss the flip and one side scorches before the center becomes tender. High heat evaporates surface moisture and starts caramelization.

Scatter the walnut pieces and pepitas between the flipped squash cubes. Return the pan to 425°F for 10 to 12 minutes. At minute 7, slide the pan forward and back once so the seeds settle into new gaps. Don't stir again. The squash needs direct contact with the pan while the nuts toast beside it. The squash should turn deep orange with dark amber corners. A fork should enter the thickest cube with slight resistance. Meanwhile, the walnuts smell toasted and the pepitas begin to pop softly. Go past 12 minutes and the nuts turn bitter while the maple burns. The final blast browns the sugars without collapsing the cubes.

Rest the pan off the 425°F oven for 3 minutes. Add the dried cranberries, chopped parsley and orange zest. Use two broad folding motions from the pan edges toward the center. Then spoon one warm portion onto a low-rimmed white plate. Keep the cubes intact and leave several cranberries visible on top. The glaze should look glossy and lightly tacky. The cranberries stay ruby and plump while the parsley remains green. You'll smell fresh citrus as the zest hits the warm squash. Toss immediately and the parsley wilts. Wait longer than 10 minutes and the glaze clumps around the nuts. A short rest thickens the glaze without dulling the garnish.