Criptext's approach is essentially to stream your email contents to you. The message looks like a regular email message (well, almost; more on that in a moment), but it is not really on your machine. The message holder is there, but the contents are streamed from Criptext's server. Because of this, there's a split-second delay when you open a message before the contents are displayed. It's not noticeable unless you're looking for it.
What this means is that you could look at that same message 50 times, and it might say different things each time, as the sender updates the file on the server. So as you and those seven other people negotiate that meeting time, the email message is constantly updated. You can leave the history intact, which is helpful as you try to coordinate a day and time when everyone is available, but once you've zeroed in on a time that works for everyone, you can zap the history and just send out the final, truly relevant information.
Oh, an aside: this system automatically encrypts all messages and all attachments — using a private AES 512 bit encryption key — and will decrypt it for anyone you send it to. (I wonder whether Hillary Clinton could have benefited from that?) According to Criptext CEO Mayer Mizrachi, "The server then shares a public RSA 2,048-bit encryption key with the user, which is used to securely transfer the unique AES 512 encryption key that encrypted the email to begin with. The email then safely reaches the user's unique box in the Criptext server."
Being able to seamlessly have all of your employees encrypting every message and attachment is compelling. Preliminary pricing from the company seems odd in that it wants to charge $50/month for "enterprises," with unlimited encrypted emails, but it doesn't define an enterprise. (Go for it, Walmart. That's quite a deal.)
The current beta-test version of the product, which I've played around with, has some logistical hurdles, but the concept is quite intriguing. Hurdle No. 1: Remember when I said it looks almost like every other message? It turns out that it's not text at all, but an image. That's a problem when you want to copy a line and use it in a document or drop some numbers into a spreadsheet. It's especially a problem when replying to a message and trying to comment on specific parts of the initial message.
Hurdle No. 2: The same capability that can make it convenient for the recipient and secure for the sender also makes it problematic for record-keeping. When you receive that final version of an important contract or a summary of what a colleague promises to deliver by next Thursday, you really want to save it and know that the sender won't be able to surreptitiously change the details. ("What are you talking about, Phil? I said I would only send you two models at that price and the rest were for 100 times that amount. Go back and reread what I sent you last week.")
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