Step 1: Preheat your oven to 400°F (200°C). Wash and pat dry the sweet potatoes. Prick them several times with a fork. Drizzle with a little olive oil, rub with salt and pepper. Place directly on an oven rack or a baking sheet and roast for 40-50 minutes, or until very tender when pierced with a fork.
Step 2: While the sweet potatoes roast, prepare the cranberry glaze. In a small saucepan, combine cranberries, granulated sugar, water, orange zest, and orange juice. Bring to a simmer over medium heat, then reduce heat to low and cook for 8-10 minutes, stirring occasionally, until cranberries burst and the sauce thickens slightly. Remove from heat and set aside.
Step 3: In a small skillet, toast the chopped pecans over medium heat for 3-5 minutes, stirring frequently, until fragrant. Be careful not to burn them. Transfer to a bowl and toss with 1 tbsp maple syrup and melted butter. Set aside.
Step 4: Once the sweet potatoes are tender, carefully remove them from the oven. Slice each potato lengthwise down the middle, being careful not to cut all the way through, creating a boat. Gently scoop out about half of the cooked sweet potato flesh from each half into a mixing bowl, leaving enough around the skin to maintain its shape.
Step 5: To the scooped sweet potato flesh, add the remaining 1 tbsp maple syrup, half of the Brie cheese pieces, and half of the maple-glazed pecans. Mash gently with a fork until just combined, leaving some texture. Season with a pinch more salt and pepper if desired.
Step 6: Spoon the sweet potato mixture back into the sweet potato skins. Top each half with the remaining Brie cheese pieces and maple-glazed pecans. Place the stuffed sweet potatoes back on the baking sheet.
Step 7: Return the stuffed sweet potatoes to the oven for an additional 10-15 minutes, or until the Brie is melted and bubbly and the pecans are golden. If you like, you can switch to broiler for the last 2-3 minutes for extra crispiness on the cheese and pecans.
Step 8: Carefully remove from the oven. Drizzle generously with the prepared cranberry glaze. Serve immediately and enjoy your ultimate fall dish!