Roast the butternut squash. Toss the butternut squash with the olive oil and spread it out onto a baking sheet tray. Place into a 400° F oven and cook for 30-40 minutes or until tender. When the squash is ready, remove it from the oven and let it cool.
Place the cranberries in a blender and add the remaining dressing ingredients. Blend well until fully mixed and no longer chunky. If the dressing is too thick, add 1-2 tablespoons of the reserved soaking liquid to thin out the dressing.