The indictment of John Bolton alleges he sent "diary-like entries" using a nongovernmental email, "such as email accounts hosted by AOL and Google," to send classified information. The prosecution’s success will depend on “what proof there is” of Bolton’s knowledge that he was using “an insecure website,” former federal prosecutor Scott Frederickson says. “It all depends on the facts. Every government official is schooled on how this works. And when you’re dealing with the highest classified doc