Flame's Windows Update Hack Wins Pwnie Award for Epic Ownage at Black Hat

The judging panel of the Pwnie Awards, which are handed out every year at the Black Hat security conference for achievements and failures in IT security, have recognized the Windows Update hack used by the Flame cyberespionage malware as the most impressive compromise of the past 12 months.

According to the Pwnie Awards website, the "Epic 0wnage" award goes to the hackers responsible for "delivering the most damaging, widely publicized, or hilarious 0wnage."

This year's nominees included:

-- the authors of the Flame malware, for coming up with a novel cryptoanalysis technique to generate a rogue Microsoft code-signing certificate that allowed them to deliver malware as a Windows update;

-- Certificate Authorities (CAs) everywhere, which were described by the Pwnie Awards judges as one massive security vulnerability because several of them were compromised during the past year;

-- and the iOS jailbreakers from the iPhone Dev Team and Chronic Dev Team, for essentially convincing millions of users to keep their devices unpatched and vulnerable to known critical flaws that are used in the jailbreaks.

The MD5 collision crypto attack used by the Flame authors to spoof Windows Update was a very sophisticated hack, said reputed security researcher and Pwnie Awards judge Alexander Sotirov at the awards ceremony. Some of the best cryptographers in the world are still trying to determine how the collision attack was actually performed, he said.

In addition to using a novel cryptoanalysis technique, this attack also had very serious implications, because it weakened the public's trust in Windows Update, Sotirov said. How can anyone trust it now, after it was abused by real attackers and not just in an academic setting? the researcher asked.

Sotirov was part of an international team of security researchers who demonstrated a practical collision attack against the MD5 algorithm in 2008 by generating a rogue CA certificate that gave them the ability to spoof any HTTPS-protected website on the Internet.

After that incident, everyone thought that vendors would stop using digital certificates with MD5 signatures, but Microsoft was still using one as of 2012, Sotirov said.

Following the discovery of the Flame attack, Microsoft revoked three of its intermediate CA certificates and strengthened Windows Update to prevent similar attacks in the future.

The Flame attack was embarrassing for Microsoft and therefore somewhat hilarious, Sotirov said.

As expected, none of the yet-unknown Flame authors showed up to pick up the award at the ceremony. However, a man of Asian descent dressed in a dark green military costume stood up from his seat in the audience to applause and laughter from other attendees.

This year's "Most Epic FAIL" Pwnie award went to security hardware vendor F5 Networks, whose devices were found to contain a SSH private key for the root account that worked on all of them.

However, the nominees in this category also included the entire antivirus industry for failing to detect threats like Stuxnet, Duqu or Flame, and LinkedIn for suffering a data breach that resulted in the theft of 6.5 million easily crackable password hashes.

The Pwnie award for best client-side bug went to vulnerability researchers Pinkie Pie and Sergey Glazunov, for their respective Google Chrome sandbox escape exploits presented at the CanSecWest security conference earlier this year.

Security researcher Sergei Golubchik won the Pwnie award for best server-side bug after discovering a flaw in MySQL that allowed attackers to bypass authentication by repeatedly trying to log in with bad passwords.

Security researcher Mateusz Jurczyk, also known as "j00ru," won the Pwnie for the best privilege escalation bug for finding a vulnerability in the Windows kernel that affected all 32-bit versions of Windows.

The Pwnie award for the most innovative security research went to security researcher Travis Goodspeed for developing a method of sending data packets over the Internet that can inject additional packets into internal networks.

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