Make the Orange Glaze - In a small bowl, whisk together the melted butter, honey, orange zest, orange juice, apple cider vinegar, thyme, black pepper, and cinnamon. Set aside.
Cook the Butternut Squash - In a large sauté pan, heat 1 tablespoon olive oil over medium heat. Add the butternut squash and ¼ teaspoon of salt, stir to coat in the oil, and spread out in a single layer. Cook for 5 minutes without stirring so the pieces begin to brown lightly. Stir and redistribute the pieces, cooking for 5 minutes. Stir again and cook until the squash is fork-tender, about 15 minutes total. Remove the squash from the pan and transfer to a bowl. Reserve the pan.
Blanch the Brussels Sprouts - Bring enough salted water to cover the Brussels sprouts to a boil. Add the halved sprouts and cook until tender, about 5 to 6 minutes. Drain well and shake off excess water.
Brown the Brussels Sprouts - Heat 1 tablespoon of oil over medium heat in the same pan used to cook the butternut squash. Sear the blanched sprouts cut side down until browned, about 3 minutes. Turn over and sprinkle the sprouts with ½ teaspoon of salt and cook for 3 minutes until browned.
Add the Orange Glaze - Reduce the heat to low and add the butternut squash back to the pan. Add the orange glaze and stir to combine. Season with more salt and pepper if desired.
To Serve - Stir in the cranberries and pecans right before serving and enjoy warm.
Notes
Storing: Store in an airtight container in the refrigerator for up to 3 days.
Reheating: Microwave in 15 to 30-second increments until warmed.