fileprivate protocol Wrapper {
  static func baseType(level: inout Int) -> Any.Type
  func baseType(level: inout Int) -> Any.Type
}

extension Optional: Wrapper {
  fileprivate static func baseType(level: inout Int) -> Any.Type {
    level += 1
    switch Wrapped.self {
    case let wrapper as Wrapper.Type:
      return wrapper.baseType(level: &level)
    default:
      return Wrapped.self
    }
  }

  func baseType(level: inout Int) -> Any.Type {
    level += 1
    switch self {
    case .some(let wrapper as Wrapper):
      return wrapper.baseType(level: &level)
    case .some(let wrapped):
      return type(of: wrapped)
    case .none:
      return Optional.baseType(level: &level)
    }
  }
}

let wrappedValue: String? = "Swift"
let test_1: Any?? = wrappedValue
let test_2: Any?? = Optional(wrappedValue as Any)

var level = 0
// THIS SHOULD BE `String 2` not `Any 2`
print(test_1.baseType(level: &level), level) // prints `Any 2`

level = 0
print(test_2.baseType(level: &level), level) // prints `String 3`