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Despite the attention that is now being paid to topics such as cookies, advertisements, and anonymous browsing, these are all relative newcomers to a privacy issue that dominated the field of internet security for much of the 1990s—the sending of encrypted email.
Today, email carries some of our most confidential information. Yet basic email, as a communications medium, is riddled with poor security. Consider these potential email threats:
By sending an email message, you might reveal your
Your email message might be
Your email message could be delivered to the wrong recipient, either because of an error with the mail system, or because you inadvertently selected the wrong recipient from your mail program's address book.
Your email message could "bounce" into a
Once your email message is delivered, it might be seen by someone other than the intended recipient. (For example, somebody could gain unauthorized access to your correspondent's computer, or the message might be turned over to an attorney as part of a discovery process.)
The intended recipient might forward the email message to someone against your wishes.
You might leave a job where you had been using your old email address for both business and personal email. Your former employer decides not to forward your old email to your new address, but to have it bounce—or,
Your email might be maliciously edited while it sits on your correspondent's mail server, before it is picked up by the intended recipient.
Some of these threats may seem improbable, but in fact every one of these threats has
At the same time, none of these threats are insurmountable; all of them can be
One of the simplest ways to improve your email privacy is to use a web-based email provider. These systems provide free or low-cost email accounts that you can check from
 Other good choices for semi-permanent email addresses are professional organizations and university alumni organizations, many of which now offer "email forwarding for life." Instead of providing mailboxes, these organizations provide email addresses that you can set up to forward to a specific ISP or web-based email provider that you happen to be using at a particular time.
Web-based email systems are not without their dangers. Some of the problems that you may encounter with these systems include:
Using these services gives the email provider complete, unrestricted access to your email. For many people this isn't an issue, but for some it's a serious concern.
Few of these services have provisions for encrypting email. As a result, there are no protections against mail that is
As most of the email providers do not support SSL encryption, your mail is susceptible to interception by a network monitoring device located on your local area network or at your ISP.
Some of the web-based providers will attach advertisements to the bottom of your outgoing email messages.
Despite these drawbacks, the careful and selective use of web-based email can dramatically improve email privacy for many individuals. And because it takes less than five minutes to set up a free email account, web-based systems make it practical to create an email address for a single purpose, use it, and then discard it.
Hushmail is a web-based email provider with a difference (see Figure 10-10). Unlike Hotmail, Yahoo Mail, and the others, Hushmail encrypts all email messages passing through the system so that the messages cannot be read by anybody, not even by Hushmail's staff. Unlike other web-based mail systems, even if Hushmail is
Hushmail can provide this level of security because the unencrypted email messages are never present on the company's servers. That's because Hushmail's encryption doesn't take place on the Hushmail servers—it takes place instead on each user's computer (see Figure 10-11).
When you sign up for Hushmail, the Hushmail web server downloads a Java application to your computer. The first thing this application does is to create a public key and a private key. The private key is encrypted with your passphrase, and then both keys are uploaded to the Hushmail server. The
Hushmail is as easy to use as other web-based mail systems. The encryption is completely automatic. When you send email to another Hushmail user, the system automatically downloads the user's key from the Hushmail server and uses this key to encrypt the message that you are sending them. When you are sent encrypted mail, the system automatically decrypts the message before displaying it. 
 You can also use Hushmail to exchange email with the wider Internet, but as of May 2001 the system does not encrypt these messages. Hushmail plans to adopt the OpenPGP standard for exchanging email messages with non-Hushmail users.
While Hushmail is easy to use, the fact that the unencrypted messages never appear on Hushmail's servers makes the system very secure. And because the Hushmail messages are decrypted in a Java application and displayed on the screen, the unencrypted messages are likewise never stored in a file on your computer's hard disk (unless you explicitly copy a message and save it).
As of the spring of 2001, Hushmail offers two different kinds of personal accounts: an advertising-subsidized free service, which provides users with full encryption and 5 megabytes of online mail storage, and a "Premium" version that includes 32 megabytes of mail storage and no banner advertisements.
With many modern computer systems, throwing away a piece of email can frequently be more difficult than holding onto it. A typical email message is copied at least four times during the course of its life. There is the original copy that is made for the person who
These multiple copies of email messages on different computer systems can be a boon to
Because of their candor, detail, and voluminousness, email messages are now routinely sought in divorce
In a free and
Omniva Policy Systems is an email destruction system that overcomes this seemingly
When the recipient of the message
Omniva email is not perfect. Forwarded email messages retain the self-destruction capability, but if you manually copy a message out of a window and paste it into a second, the new message will not automatically self-destruct. You can always print an email message, and unless you then shred the paper, the printed copy will be around for a long time. But the Omniva email system does make it possible for
Furthermore, the Omniva email system does significantly increase the privacy that is afforded to email users, because email messages that are accidentally bounced into postmaster's mail boxes or saved on magnetic backup tapes are unintelligible without the decryption key.
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