For the Salad:

1. Preheat the oven to 400°F and line a large baking sheet with parchment. Add the cubed squash, spreading it out in an even layer. Drizzle over the olive oil, salt, pepper, and cinnamon. Stir the squash on the pan until it is evenly coated in the oil and seasonings.
2. Roast the squash for 15-20 minutes or until tender and caramelized in spots.
3. Meanwhile, cook the couscous by heating a medium saucepan over medium heat. Add a tiny drizzle of oil to the pan and then add the couscous.
4. Cook, stirring constantly, until it is lightly browned and toasted in spots, about 2 minutes.
5. Add 3 cups of water and 1 teaspoon of salt. Bring the water to a boil. Reduce the heat to low and cover the pot.
6. Simmer over low heat for 15-20 minutes, or until the water is mostly absorbed and the couscous is fluffy and tender. Drain off any excess liquid.

For the Vinaigrette:

1. While the squash is roasting and the couscous is cooking, make the vinaigrette by whisking the apple cider, mustard, vinegar, honey, and cinnamon together in a large measuring cup.
2. Whisking constantly, slowly stream in the oil until the dressing is emulsified and thick. Season, to taste with salt and pepper.

To Assemble & Serve:

1. Add the warm couscous to a large mixing bowl, drizzle over roughly ½ of the vinaigrette, and toss well to combine.
2. Stir in the roasted squash, apples, baby arugula, cranberries, pepitas/nuts, and toss to combine.
3. Season, to taste, with salt and pepper. Drizzle with more dressing, if you prefer.
4. Serve immediately while still warm, at room temperature, or chilled.