Encryption probably raises a big red flag, and they likely have stuff in place that will blow right through it. Obfuscation of some kind might be a better bet, but they likely have technologies that can sniff that out as well.
Myself, I’m gonna start using carrier pigeons!
Encrypted emails and communications go across worldwide networks every second. I guarantee you that it doesn’t raise any red flags, and I urge you to look into it.
With a 2048 bit certificate, it would take the world’s most powerful computer arrays over a decade to crack the encryption. There’s no real way to “blow right through” a securely encrypted message. Unless they really want to know what you’re communicating to your old aunt Bess, they’re going to put off trying to brute-force your encryption hash and dedicate computing resources to the Mohammeds and Husseins of the world for now.
The quickest and cheapest way you can protect yourself right now is to use a password locker that encrypts itself (I like KeePass). Assign the database a complex password that you can remember (hint: use spaces and characters in the password to add complexity), and then have the password locker assign random character passwords for all of your accounts to prevent brute force and dictionary attacks on your stuff. You can load the program and the database on a secure, encrypted thumb drive and anytime you need to login to something while you’re away from home, just open it up and have it auto-populate your password fields.
We live in a world where just having a simple “ILoveMom” or “Passw0rd1234” passwords don’t cut the mustard. There are entire botnets dedicated to brute force attacks on Facebook, Twitter, video game networks, and even corporate webmail portals. Protect yourself and learn some basics to keep a leg up on the “script kiddies” who want to defraud you.
Myself, I’m gonna start using carrier pigeons!
It's pretty clear that what the government flags for review is certain words or phrases (they can't very well have a human look at the billions of emails every day). For example, an email discussing the purchase of an AK-47 and 2,000 rounds of ammo at the "gun show" is going to get looked at because the system flagged "AK-47", "Ammo" and "gun show". However an email talking about the purchase of a "Russian Hammer" and 2,000 "nails" at the "hardware store" wouldn't even get a second glance.
Of course both you and your recipient would need to have an understanding before hand that when you talk about certain topics (in this case guns) that you will use code.