Heat a large soup pot over medium heat. Add the olive oil. Once hot, add the onions and a pinch of brown sugar. Season with a little salt and pepper. Cook about 5 minutes, stirring frequently, until softened. At this point, slowly add in the apple cider, let it cook into the onions, add more and continue to cook. Do this until the onions are caramelized. Add the apples and thyme to the pot and cook over medium heat, stirring, until softened, 8 minutes. Add in any remaining apple cider, the beer, chicken broth and cayenne. Bring to a simmer and cook 5-10 minutes or until the apples are tender. (This is when I bake the crumble)
Meanwhile, whisk the flour into the milk until smooth. Set aside.
Once the apples are soft, puree the soup until chunky smooth or completely smooth (whatever you like). Return the soup to the stove and bring to a low bowl. Whisk in the milk mixture and boil until the soup thickens slightly, about 5 minutes.
Stir in the cheddar cheddar cheese and brie until melted and smooth. Simmer the soup 5 minutes or until ready to serve.
Ladle the soup into bowls and top with the cinnamon pecan crumble. Plus maybe some extra cheese too!! Happy slurping!