Preheat oven to 375°F and line a baking sheet with parchment paper
To a medium bowl add squash, three tablespoons oil, salt and pepper. Toss to coat. Spread out in a single layer onto prepared baking sheet. Transfer to oven and roast until squash is fork tender and golden brown, about 20 minutes.
To a large skillet set over medium heat add remaining one tablespoon olive oil. When oil is shimmering add red onion, cook until onion is tender and translucent, about 5 minutes. Add in cranberries and thyme, cook until the cranberry skin begins to pop open, about 5 minutes.
Transfer roasted squash into skillet with cranberries, stir to combine. Taste and adjust seasoning.
To serve: Scoop vegetables onto a platter, serve immediately.
