Heat oven to 400 degrees F (204 C) — use the convection setting if you have it for crispier sprouts. Also line a baking sheet with parchment paper. Set aside.
Add balsamic vinegar to a small saucepan and bring to a very low boil over medium heat. Then reduce heat slightly (medium low to low) to a steady simmer (bubbles should be consistently forming around the sides and in the center of the pot — but not a full boil). Continue cooking until reduced by half and the vinegar leaves a thin film on the bottom of the pan when tipped to the side, ~15-20 minutes. Watch carefully toward the end to ensure it doesn’t burn.
Pour balsamic reduction into a serving dish to cool. It will continue to thicken into a caramel-like syrup. Set aside for serving.
Halve Brussels sprouts and add to a large mixing bowl. Add half of the oil (1 tsp as original recipe is written) and salt and pepper and toss to combine.
OPTIONAL: For extra crispy sprouts, heat a large (oven-safe) pan (preferably cast iron) over medium-high heat. Once hot, add a drizzle of oil (remaining 1 tsp as original recipe is written)and swirl pan to coat. Add half of the Brussels sprouts (or as many as will comfortably fit in the pan) cut-side down and sear for 3-4 minutes, or until light golden brown on the underside. Then transfer the pan to the prepared baking sheet. Repeat this step (adding more oil to the pan as needed) until all sprouts have been seared and are on the baking sheet.
Add the crushed garlic to the baking sheet with the sprouts and toss. Spread into an even layer and roast for 10-12 minutes, or until sprouts are golden brown and tender. Bake longer for crispier sprouts.
Transfer sprouts to a serving platter and top with spoonfuls of dairy-free cheese and dried cherries. Drizzle with some of the balsamic reduction, or serve on the side.
Store cooled leftovers covered in the refrigerator for 1-2 days, though best when fresh. Reheat on the stovetop over medium heat, or in a 375 degree F (190C) oven until hot. Not freezer friendly.
*Nutrition information is a rough estimate calculated with half of the balsamic reduction (there will likely be some left over). *If oil-free, check out our Guide to Oil-Free Roasted Vegetables!