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Preheat the oven to 425°F (220°C). Line two baking sheets with parchment paper.
Toss the butternut squash with olive oil, maple syrup, cinnamon, thyme, salt, and black pepper. Spread in a single layer and roast for 20–25 minutes, until tender and caramelized. Let cool slightly.
Reduce the oven temperature to 400°F (200°C). Unroll the puff pastry and cut into 9 equal squares. Place them on the prepared baking sheet.
Lightly score a smaller square inside each pastry piece, leaving a ½-inch border. Do not cut completely through the pastry.
Spoon a small amount of cranberry sauce into the center of each square. Top with roasted butternut squash and pieces of Brie.
Brush the pastry borders with beaten egg.
Bake for 18–22 minutes, until puffed, crisp, and deeply golden and the Brie is melted.
Combine the cranberry sauce, maple syrup, orange juice, orange zest, and cinnamon in a small saucepan. Warm over low heat for 2–3 minutes, until smooth and glossy.
Toast the walnuts in a dry skillet over medium heat for 3–4 minutes. Add maple syrup and sea salt, stirring for another minute until lightly caramelized.
Drizzle the warm cranberry glaze over the pastry squares and finish with toasted walnuts, dried cranberries, thyme, and pomegranate seeds if using. Serve warm.