Prepare the Oven and Baking Sheet: Preheat the oven to 425°F (220°C). Position a rack in the center of the oven. Set out a large, rimmed 18 × 13-inch baking sheet so the squash can roast in a single layer.

Peel and Cube the Butternut Squash: Trim both ends of the squash and peel away the tough outer skin. Cut it in half lengthwise, scoop out the seeds, and cut the flesh into ¾-inch (2 cm) cubes. Aim for evenly sized pieces so they cook at approximately the same rate. You should have about 2 pounds (900 g) of prepared squash.

Season the Squash: Place the cubed squash in a large mixing bowl. Add 2 tablespoons olive oil, ½ teaspoon fine sea salt, ¼ teaspoon black pepper, and ½ teaspoon ground cinnamon. Toss until the cubes are evenly coated with a thin, glossy layer of oil and seasoning.

Arrange the Squash for Roasting: Spread the seasoned squash across the baking sheet in one even layer. Leave a little space between the pieces wherever possible. Overcrowding traps steam and can prevent the edges from browning.

Roast Until Golden and Tender: Roast for 25–30 minutes, turning the squash with a spatula after approximately 15 minutes. The pieces should be lightly browned along the edges and tender enough for a fork to slide through easily. If the squash is still firm, continue roasting for another 3–5 minutes, checking frequently.

Prepare the Maple-Balsamic Dressing: While the squash roasts, whisk together 1 tablespoon maple syrup, 1 tablespoon balsamic vinegar, and 1 tablespoon extra-virgin olive oil in a small bowl. Continue whisking until the dressing looks glossy and temporarily blended. It should be thin enough to drizzle easily.

Let the Squash Cool Briefly and Add the Cranberries: Remove the baking sheet from the oven and allow the squash to cool for 5 minutes. Transfer it to a wide serving bowl or platter. Add ½ cup dried cranberries and 1 tablespoon of the fresh thyme leaves. Gently toss to distribute the ingredients without breaking apart the tender squash.

Add the Dressing and Feta: Drizzle the maple-balsamic dressing over the warm squash and gently fold once or twice to coat. Sprinkle ½ cup crumbled feta evenly over the top. Avoid vigorous stirring, which can break down the cheese and make the squash look mashed.

Garnish and Serve: Finish with the remaining 1 tablespoon fresh thyme leaves and the optional ¼ cup toasted chopped pecans. Serve warm or at room temperature. The squash should be tender, with caramelized edges, while the cranberries provide chewiness and the feta remains creamy and distinct.