I wish there was a router that could automagically handle encryption. This way even grandma could plug in her "freedom box" behind her router and have secure communications. Maybe a simple web based admin page to manage configuration.

Would love to see this, i.e. some open source box, that just handles OpenVPN and TrueCrypt for the local network. As an idea it sounds not that overtly complex to realize - just hoping somebody will take something like this one day on Kickstarter.

That sounds very hard. How does it know to encrypt my Google docs, but not my public tweets?

Specifically encryption using your own key that you never transmit to a third party/your cloud provider.

I'm hoping web crypto will solve this, but only if the e-mail and storage service providers offer the option in an intuitive way, and I don't think the big ones like Google and Microsoft will want to do that unless we all demand it. It's also not going to be a finished draft until 2014, so we have to wait a little more.

http://www.w3.org/2012/webcrypto

Web crypto will never solve this, especially not when provided by a big company like Google/MSFT. They'll always have provisions to make the unencrypted version available to authorities. You can only trust client side encryption.

Yes, that's what I meant. Implement web crypto and allow the user to use his own encryption key. So nobody but you and the recipient can access it (unless they can crack it, of course).

If you do that "the cloud" can do nothing with that data. You wouldn't be able to search your gmail account without storing it all offline unencrypted. The only cloud service that just about works with encryption is backup.

Not necessarily... My pitiably incomplete understanding of something called "fully homomorphic encryption" is that it offers the possibility of letting someone else do operations (math, search, etc) on your encrypted data, giving you useful results, without them ever actually seeing the plaintext data.

My understanding is that this is still in the experimental stage.

My understanding of encryption is probably no more complete than yours, but any operation that can give me useful search results necessarily reveals a lot about the content. That's the point of search after all.