We’ve all sent email that, on second thought, would have best been sent to the trash folder rather than out into the world. On occasion, you might also pine for a way to prevent recipients from forwarding or showing important or sensitive messages to others.

So-called “self-destructing” email services provide options to recall messages, as well as dictate who sees them and for how long. These services are far from perfect, but sometimes it’s useful to retain at least some control over email that otherwise would be beyond reach as soon as it left your outbox.

Control Your Sent Messages

A variety of services offer what they call secure, tracked, or self-destructing email. Some sites, such as Will Self-Destruct (www.willselfdestruct.com) and KickNotes (www.kicknotes.com), provide message recipients one-time access to a secure Web page that contains your message. Recipients get an email directing them to the page with the message, which is accessible only once. After that, the message is deleted.

Will Self-Destruct lets you send anonymous messages that can be viewed only once and then disappear after a set time period. Other email services provide tracking and other control over who reads your email and when.

Other services attempt to integrate themselves with existing email applications. The way most of these seem to work is by replacing the plain text of your email with a graphic image of the text, which is stored at the Web site’s server rather than in the email message itself. The email simply contains a link to the image file. That way, the service can exercise some control over who looks at the message, how many times, and for how long. Examples of this type of service include BigString (www.bigstring.com) and Kablooey Mail (www.kablooeymail.com).

How you send a message also varies from service to service. Some, such as Will Self-Destruct, KickNotes, and BigString work like Web mail, with a browser-based interface that you can access from any computer. Others work with your existing email client. For instance, Self-Destructing-Email.com ($3.99 per month; www.self-destructing-email.com) works equally well with any existing email program. Once you register with the site, you can send a secure message simply by adding “.self-destructing-email.com” at the end of any recipient’s email address. The email is routed through the service, converted from plain text into an image link, and forwarded using the recipient’s normal address.

Loopholes & Limitations

Absolute security cannot be assured with any of these systems. For instance, KickNotes messages are written as plain text that can be copied and pasted elsewhere by the reader. And we were able to print a copy of a (supposedly secure) BigString self-destructing email we received. Furthermore, a major loophole in the defenses of every one of these services is the ability to take screen shots of messages before they disappear.

In other words, self-destructing emails may be more difficult to copy or forward, depending on the service, but not impossible. Someone with a bit of computer experience can easily copy your message and keep it indefinitely or forward it to others. Affirmative steps would be required to do that, however, which means inadvertent forwarding or copying is much less likely.

However, going through the effort of using a more secure email system alerts your recipient to the fact that the message might be sensitive, which should raise awareness that the email is not for general dissemination. Some of these services, such as Will Self-Destruct, are also good for sending anonymous email. Tracking features can also help you determine whether particular recipients have read the message. In addition, some services allow you to recall messages that have not yet been read, which can be a lifesaver if you press that Send button a little too early.

Though you can’t count on free secure email sites to send top-secret information, they do have a use for more mundane matters if you keep in mind the limitations.

by Alan Phelps