Step 1: Preheat oven to 400°F (200°C). Line a large baking sheet with parchment paper.
Step 2: In a large bowl, toss the butternut squash cubes with olive oil, salt, and pepper until evenly coated.
Step 3: Spread the squash in a single layer on the prepared baking sheet. Ensure not to overcrowd; use a second sheet if necessary for even caramelization.
Step 4: Roast for 25-30 minutes, tossing halfway through, until the squash is tender and beautifully caramelized at the edges.
Step 5: While the squash roasts, prepare the glaze. In a small saucepan, combine cranberries, balsamic vinegar, maple syrup, water, and cinnamon (if using).
Step 6: Bring to a simmer over medium heat, then reduce heat to low and cook for 5-7 minutes, stirring occasionally, until the cranberries burst and the glaze thickens slightly. Mash cranberries lightly with a fork if desired.
Step 7: Once the squash is roasted, transfer it to a serving bowl. Pour the cranberry-balsamic glaze over the squash and gently toss to coat.
Step 8: Crumble Gorgonzola cheese over the warm squash. Garnish with fresh parsley or thyme before serving.