I worked for a courier service here in Portland for about a month. Everyone moving large files involving anything important uses sealed packages with encrypted hard drives.

I also noticed that's how it goes when I worked for an electrical company changing over a bunch of stuff in a modern movie theater. They have special packages and boxes that they use for sending new release movies back and forth with and what they do is load it into the projectors in the form of an encrypted hard drive, then go through a number of programming and password protocols online in real time to get authorization to play the show.

The spies and anarchists out of Europe have been in to using dead drops with USB thumb drives for over a decade.

Frequent use of encryption is going to attract the wrong kind of attention, the wrong kind of attention is then going to attract efforts to investigate, efforts to investigate eventually require results, the requirement for investigative results, in the police state environment, will, in the mind of the police state, require adverse action. If they don't find a reason, they will make it up, and what may have not otherwise been a priority target becomes one.

The trick is to escape the unwanted attention in the first place, with the vast majority if your communication being open, common, and innocent. Or at least open, common, and innocent sounding to those eavesdropping on it. Thus, any conclusions they come to based on whatever they seem to think is some sort of "secret code" eventually has the appearance of a wild goose chase, which it often is, and erodes their organizational credibility from within. Once their organizational credibility is eroded, their funding cuts happen from there, once their funding cuts happen, the effectiveness of your enemy and their capability for aggression is diminished.