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Fighting Spam with Exchange and Outlook 2003

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Unless you live under a rock, you likely receive spam. USA Today estimates that over seven billion spam messages will be sent out this year alone. Aside from the frustration of sorting through and deleting these messages, several legal battles are beginning to take shape. Already the ISPs are jumping in to try to stop spam at the source, but in June employees began taking their employers to court because of the pornography appearing in their email. Cisco is now involved in such a suit since it has claimed (as has most companies) that the computers and content are their property. The argument is Cisco should be more active in trying to stop unsolicited pornography and graphic pictures from coming through the email system. The results of this case will be interesting to see. Do companies have a legal requirement to fight spam?

Microsoft is also ready to stop spam. Bill Gates has offered several discussions on the matter and published a few papers on spam and the need to stop it. To prove it’s point, Microsoft has included much more sophisticated spam-fighting features in the newest versions of Outlook and Exchange. In this article we will describe these functions in detail and point out both their strengths and weaknesses.

Many of you may remember the anti-spam tools that shipped with the earlier versions of Exchange and Outlook. Outlook 98 and 2000 both shipped with a function called Junk E-Mail filters. With Junk Mail filters, an end user could identify a message as having adult content so that future messages from that person would be blocked or otherwise filtered. In addition, Outlook 98 and 2000 included a hard-coded set of words and phrases that were used to try to identify junk mail and adult content messages. For example a subject that contains ‘adults only’ would be caught and filtered. Unfortunately, this filtered required you to identify the sender after you had already received a message. In addition, a spam-sender would be identified for one user and the knowledge could not be shared easily for the other users. More importantly, the phrase and key-word database could not be changed, let alone centrally managed. Having said that, these functions were adequate then since unsolicited mail was roughly one-sixth what it is now.

I would be surprised if many of you knew that Exchange 5.5 had basic Spam-fighting tools. These reverse DNS lookup and IP blocking features were slightly improved with Exchange 2000. Reverse DNS lookup helped block messages from servers who were spoofing other domains or were not valid. Diligent administrators, who watched incoming messages, could block known spam servers. To do this effectively you needed to look at the header information within the spam messages and collect the sender server’s IP. You then added this IP in the Block IP fields within Exchange and hope the spamm’er didn’t change IP addresses. As with the Outlook features, this technique was somewhat effective several years ago.

Outlook 2003 Anti-spam tools
For those of you who ware wondering if you should upgrade to Outlook 2003, let me help you make up your mind. For starters, Outlook 2003 includes a feature that blocks html-embedded messages from automatically retrieving pictures from the Internet. This feature alone should help reduce much of the pornography that comes across in unsolicited messages. Spam’mers pay ISP costs as you and I and they can’t afford to send millions of large messages since that limits the number of people they can reach. By using this feature (which is turned on by default) messages that get through probably won’t contain graphics. This new feature could have probably helped out the case now pending at Cisco. While this feature does in effect block linked graphics, it will not help if the image is sent with the message. Nor will this feature block bold, flashing, offensive text. 

Fighting Spam with Exchange and Outlook 2003
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Copyright Stephen Bryant 2008