In the context of pattern matching, x? is the “optional pattern” and equivalent to .some(x). Consequently, case x?? is a “double optional pattern” and equivalent to .some(.some(x)).
It is used here because UIApplication.shared.delegate?.window evaluates to a “double optional” UIWindow??, compare Why is main window of type double optional?.
Therefore
if case let presentationAnchor?? = UIApplication.shared.delegate?.window
matches the case that UIApplication.shared.delegate is not nil and the delegate implements the (optional) window property. In that case presentationAnchor is bound to the “doubly unwrapped” UIWindow.
See also Optional Pattern in the Swift reference:
An optional pattern matches values wrapped in a some(Wrapped) case of an Optional<Wrapped> enumeration. Optional patterns consist of an identifier pattern followed immediately by a question mark and appear in the same places as enumeration case patterns.