The real work is done in checkDynamicCastFromOptional. This code tried to unwrap the source and returned the payload on success. It only did this once, so a type like Optional<Optional<Int>> would come out as Optional<Int> and then a cast to Int would fail.
This change makes checkDynamicCastFromOptional recursive, which makes it unwrap as many levels of Optional as it encounters.
Fixes rdar://problem/40171034 and SR-7664.