Preheat oven to 425°F. Coat a baking sheet with nonstick spray.
Toss sweet potatoes with oil, 1½ teaspoons salt, and 1 teaspoon paprika in a bowl; season with black pepper. Arrange potatoes in a single layer on prepared baking sheet, do not wash bowl. Roast sweet potatoes until nearly fork-tender, 20–25 minutes.
Meanwhile, in same bowl whisk together maple syrup, molasses, mustard, orange juice, all-spice, cinnamon, espresso, cayenne pepper, remaining ½ teaspoon salt, and remaining 1 teaspoon paprika.
Scoop potatoes into bowl with maple syrup mixture and toss to coat. Transfer potatoes back to baking sheet and roast 5–8 minutes more, tossing every few minutes, until caramelized and tender.
Transfer to a serving dish and drizzle with olive oil.