How does that work with in combination of freedom of speech? Is it one of those cases, where someone has to be brave/foolish enough to disobey and take it to the supreme court?
> How does that work with in combination of freedom of speech?
The government is not preventing you from expressing your free thoughts and opinions. They are compelling you to not disclose the details of something you had no knowledge of before they asked you about it.
Nothing is stopping you from writing a blog post about how it is unfair to seek records of a potential criminal, but you cannot write about how it is unfair to seek the records of Bob Jones when you had no other reason to believe Bob was anything but a regular user.
Most likely... but the party who was served the order can file for appeal if they are willing to go that route. That said, it doesn't mean any such appeal with favor the party served the gag order.
And the case likely was "we swear it is very important for national security, trust us!" and that was enough. Search request is almost never refused, e.g. FISA court approves over 99% of them. And if the court already deemed the proof strong enough to do the search, surely it's strong enough to put a non-disclosure on it if asked.