Preheat the oven to 375 degrees F and line a baking sheet with parchment paper.
Combine the ketchup, cranberry sauce and jalapeno in a small saucepan over medium heat. Bring to a simmer and let cook, stirring occasionally, 2 to 3 minutes. Remove from the heat, then discard the chile and set aside.
Heat 1 tablespoon olive oil in a medium skillet over medium heat. Add the onion and celery and cook until both soften and start to become translucent, 3 to 4 minutes. Add the garlic and cook for another minute. Remove from the heat and allow to cool slightly.
Combine the turkey, stuffing mix, eggs, 1 teaspoon salt and 1/2 teaspoon pepper in a large bowl. Add the onion mixture and 1 cup of the ketchup sauce and stir gently until just combined, making sure not to overmix.
Transfer the mixture to the prepared baking sheet and shape it into a loaf. Pour the remaining ketchup sauce over the loaf and spread so that the entire loaf is covered with sauce. Bake for 30 minutes.
Meanwhile, toss the sweet potatoes in a bowl with remaining tablespoon oil. Sprinkle with salt and pepper. Remove the meatloaf from the oven and scatter the wedges on the baking sheet around the meatloaf. Return to the oven and cook for another 45 minutes. Remove from the oven and let rest for 5 minutes, then slice and transfer to a serving platter. Surround with the baked sweet potatoes.