
Encryption scares a lot of people - me included - because it's based on really complicated mathematics. Thankfully, the state of encryption software has advanced sufficiently in the last couple of years that it's pretty easy for laypeople like us to take advantage of the protection it offers. Just like you don't shop online without a secured HTTPS connection, you really ought not engage in private conversations online without encrypting your messages.
The problem with email encryption is that your recipient has to be able to de-crypt it. This means that they must get your public key and then use it to de-crypt it. Until we develop a system where public keys are retrieved and cached automatically and transparently email is going to remain a largely clear text activity and never a private means of communication.
Another problem is we do encryption at the wrong level for just using as a method of secure (if not necessarily private) point to point communication (which is why it cannot replace fax machines). It should be possible to form an email address with a flag to encrypt an email during transit - for instance instead of example@example.com you would send it to example@$example.com. This would tell your SMTP server that you wish this message to be encrypted. Your SMTP server would check a cache of public keys to see if it has the one for example.com. If not it would then contact SMTP server (or perhaps a key server) for example.com who would send your server its public key (perhaps via SSL as a verification method). Your server then encrypts the message and sends it. When example.com receives the message it decrypts it and the puts it in the mailbox for the recipient. This would provide method of secure communication across the Internet that is transparent and easy to use by the average user.
We have the technology, just not the infrastructure.
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