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Microsoft: bolstering legitimacy in next-generation e-mail

In the forthcoming version Microsoft Outlook client, the software giant will introduce Microsoft SmartScreen, a new e-mail postmarking built-in technology that will be able to screen outgoing messages that individual users send. If content that may trigger anti-spam heuristics is detected, Outlook will then perform a computation that may take a few seconds of computer time to create a postmark on this message.

Volume e-mailers would not be able to tolerate this extra time overhead – several seconds per message across multimillions of messages per hour creates an unacceptable burden; but for an individual sender dealing with personal volumes of e-mail, a message sitting in an outbox folder a few extra seconds before being picked up by the server is not an issue.

This isn’t an anti-spam technology per se. It is an anti-false positive technology: when the anti-spam technologies on the edge of incoming domains see this postmark — assuming they incorporated support for this new Microsoft technology — they can then use the existence of this postmark as an indication that the message probably isn’t spam after all. The presence of the postmark will have some weight in offsetting the spaminess score assigned by the anti-spam filter based on content alone. Therefore, the technology should reduce the chance of a legitimate end user message being filtered out by spam filters due to content.

This is a very good approach. False positives for users are increasingly problematic and there really is no good alternate solution for dealing with the issue of false positives for low-volume senders. In the world of high volume senders, certifying e-mail is an option that assures delivery via the presence of a cryptographically secure tokens attached to the e-mail of qualifying, legitimate senders with the best e-mail practices and solid e-mail reputation.

Postmarking to reduce false positives is not Microsoft’s only good move in support of legitimacy. Microsoft also announced that Live Mail — the successor to Hotmail — would, under certain circumstances, feature an unsubscribe request button. Leveraging an Internet standard known as RFC 2369, unsubscribe is a major step in limiting not false positives but rather in limiting false spam complaints.

How it works: if I am a Windows Live Mail user who is getting e-mail from a legitimate volume sender which I have previously added to my “allow email from” list, instead of a “report as spam” button option showing up in the Windows Live Mail interface, I instead will see an “unsubscribe” button option. Assuming the volume sender in question is supporting this standard (they must use the List Unsubscribe header defined in RFC 2369), I can click this unsubscribe button and rather than generating a complaint (as would happen if I were clicking a “report as spam” button), I generate a request that is forwarded back to the sender to unsubscribe me.

While perhaps obvious on the surface, this is actually quite forward-thinking on Microsoft’s part and represents the first time that an ISP has taken a proactive step toward truly understanding recipient intent and communicating it back to the sender. The problem with the “report as spam” button has been that it is a one-size-fits-all solution. Individuals tend to click this button not only when they believe a message is spam, but also when they don’t like a message, when they feel they are getting too much mail from a sender, when they feel they are getting too much mail in general, or when they are just in an ornery mood.

An added benefit of the unsubscribe button is that it bolsters the legitimacy of spam complaints, since it will siphon off those complaints that are really more appropriately seen as unsubscribe requests. There are certainly some details that need to be worked out, but in general Microsoft’s movement toward greater recipient feedback granularity helps improve the experience of all players in the e-mail ecosystem, and raises overall legitimacy.

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