1. Preheat oven to 450°.
2. Place sweet potatoes on a large jelly-roll pan. Drizzle with 2 tablespoons oil, and sprinkle with salt and pepper; toss to coat. Bake at 450° for 30 minutes or until tender, turning after 15 minutes.
3. Place remaining 1 tablespoon oil, cranberries, water, and honey in a saucepan. Remove 1 or 2 chiles from can; finely chop to equal 1 tablespoon. Add chopped chipotle and 1 teaspoon adobo sauce to pan (reserve remaining chiles and sauce for another use). Place pan over medium-low heat; bring to a boil. Cover, reduce heat, and cook 10 minutes or until cranberries pop, stirring occasionally. Remove from heat. Mash with a potato masher or fork until chunky.
4. Place pepitas in a medium skillet; cook over medium heat 4 minutes or until lightly browned, shaking pan frequently.
5. Combine potatoes, pepitas, onions, and cilantro in a bowl. Add cranberry mixture to bowl; toss gently to coat.
Be sure to let the cranberries cook long enough that they start to pop; the juice helps to thicken the dressing.