There are many obvious cases that have made it to the Supreme Court. All it takes is a pig headed state or federal attorney general who insists on trying to uphold oppressive laws.
This is what the Yahoo attorneys were told in one of the few partially declassified FISA court hearings by the judge when they tried to push back on a sweeping warrant, which I believe involved full emails/information for not only a group of individuals but every person they talked to 2 hops, which quickly turns into thousands of people and companies.