Preheat the oven to 375 degF.

Trim/clean the Brussels sprouts, then cut them in half. Arrange on 2 baking sheets and toss with the olive oil. Roast until brown, 25 to 30 minutes.

Combine the balsamic vinegar and sugar in a saucepan. Bring to a boil, then reduce the heat to medium-low and reduce until very thick.

Drizzle the balsamic reduction over the roasted sprouts, then sprinkle on dried cranberries.