"It's not like locking your money in a safe, where you can feel the heaviness of the door and hear the clank of the lock." I think the perfect is being the ene

"It's not like locking your money in a safe, where you can feel the heaviness of the door and hear the clank of the lock." I think the perfect is being the enemy of the good here. Personally I would pay for a really good UI for doing that -- just encrypting files so I can stash them safely in cloud storage or transfer really sensitive stuff. I'd love to be able to right-click and encrypt/decrypt with a GPG public key or symmetric passphrase. I have full disk encryption, but that's very coarse-grained. Unlock the machine and it's defeated. My hack right now is to use encrypted OS X .sparseimage files, but that's OS-specific and clunky. I also have these scripts: https://raw.githubusercontent.com/zerotier/ZeroTierOne/master/attic/encrypt https://raw.githubusercontent.com/zerotier/ZeroTierOne/maste... https://raw.githubusercontent.com/zerotier/ZeroTierOne/master/attic/decrypt https://raw.githubusercontent.com/zerotier/ZeroTierOne/maste... They kind of suck but do the job in a platform-independent way. They could be made slightly better by trying to secure-erase the original source file, etc., but they work. The other problem with invisible omnipresent encryption is that it lacks a quality that I call "situational awareness." I like knowing that something has in fact been encrypted. Seeing a file extension change, like gzipping a file, tells me that yes in fact something has happened. A classic example I use of poor situational awareness in security is IPSec encryption setup between two boxes. The only way I know of to verify that the traffic is actually encrypted is to tcpdump the raw interface and look. The (piss-poor) IPSec tools do not really tell you this in a non-confusing straightforward way.