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Spear-Phishing Experiment Evades Big-Name Email Products

Phony 'Bill Gates' LinkedIn invitation dupes Microsoft, Cisco email products and other security tools, services

The researcher who conducted a successful spear-phishing experiment with a phony LinkedIn invitation from "Bill Gates" has revealed the email products and services that failed to filter the spoofed message -- and that list includes Microsoft Outlook 2007, Microsoft Exchange, Outlook Express, and Cisco IronPort.

Joshua Perrymon, CEO of PacketFocus, had previously revealed that the iPhone, BlackBerry, and Palm Pre smartphones had all fallen victim to the spear-phishing exercise.

"Email-based attacks are probably one of the most effective in today's hacker bag of tricks. The email security industry gets by with stopping most spam and known phishing attacks," Perrymon says. "The problem lies in a directed, under-the-radar, spear-phishing attack -- the type where the attacker spends time to understand the target, create an effective spoofed email and phishing site, [and] then attacks."

The experiment was aimed at measuring the effectiveness of email security controls in several major products and services. And the simplicity and success of the test demonstrated just how powerful social engineering can be and what little technology can actually do about it, security experts say.

Perrymon sent his spoofed LinkedIn email -- which looked a lot like a real LinkedIn invite, except it spelled the social network "LinkedIN" in the "from" field of the message -- to a variety of users in different organizations who had agreed to participate in a test. The message read: "Bill Gates has indicated you are a fellow group member of Microsoft Security. I'd like to add you to my professional network on LinkedIn. - B. Gates."

He was able to get his spoofed message through to the recipients 100 percent of the time, and across a wide range of major email products and services in addition to the Microsoft and Cisco products, including users with GoDaddy's hosted email, Voltage, RackSpace/MailTrust hosted email, Webroot SaaS Email Security, Verizon Email Cloud Filtering with MessageLabs, a Linux and SpamAssassin configuration, SonicWall's Email Security appliance, LinuxMail with greylisting, Opera Mail, and Mozilla Thunderbird, according to a report that he has now posted online.

Microsoft and Cisco had not responded to media requests for comment on the report as of this posting.

In the report, Perrymon says the research shows that even the most current email security appliances, services, and clients can't detect spear-phishing messages, "even when the senders email (From:) does not match up with the sending email server (Spoofed). For now, the user must make the decision to identify and properly respond to directed email attacks."

The underlying problem, he says, is that email security products and services rely on blacklists. "The phishing sites are being brought up instantly on a 'new' server that has not seen Internet traffic and is not on any blacklist," he says.

Perrymon says he contacted all of the affected vendors and discussed mitigation strategies with some of them. Some told him they were looking into the issue, while others noted the problem is within email itself and requires a new protocol to provide real security, Perrymon says.

Meanwhile, PacketFocus recommends organizations create email policies that describe the risk and how to mitigate it; provide a quick desk reference for users on how to identify and respond to phishing attacks; provide regular training for new hires and existing employees; use an incident response system that lets users report potential attacks and that tracks activity; and have a browser update program that ensures holes are patched immediately.

Have a comment on this story? Please click "Discuss" below. If you'd like to contact Dark Reading's editors directly, send us a message.

Kelly Jackson Higgins is Executive Editor at DarkReading.com. She is an award-winning veteran technology and business journalist with more than two decades of experience in reporting and editing for various publications, including Network Computing, Secure Enterprise ... View Full Bio

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