Add red wine, brandy, brown sugar, cloves, star anise, 4 cinnamon sticks, and cranberries to a Dutch Oven.

Use a Chef Knife to slice 2 oranges into rounds and slice the third in half. Add half of the rounds to the mulled wine and reserve half of the rounds for garnish. Squeeze the halved orange into the wine mixture.

Warm the mulled wine over medium heat until steaming, about 5 minutes, stirring to make sure sugar has dissolved. When you start seeing the tiniest of bubbles at the surface, reduce heat to low.

Carefully taste, and add another tablespoon of sugar, if necessary. Continue cooking over low heat until thoroughly warmed through,  5–10 more minutes.

Ladle the mulled wine into Coffee Mugs. Garnish each with a reserved orange round and cinnamon stick, if desired.