Bad Security Week for Apple

Public embarrassment at a hacking contest and vulnerability disclosures for a new browser made for a discouraging week for Mac security folks.

It was one security embarrassment after another for Apple the week of March 24.

It began at the CanSecWest show, where the annual hacker contest challenged attendees to compromise a Vista system, a Ubuntu Linux system and a MacBook Air. The first day was reserved for preauthentication attacks and would have netted $20,000, but nobody took the prize.

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On the second day, attackers were allowed to use default-installed client applications. Within minutes of the opening of the second day, the Mac was hijacked by security researcher Charlie Miller, who won the machine and a $10,000 prize for his efforts. Miller attacked the brand new Safari 3.1 browser through a new vulnerability, the details of which he declined to provide. The Vista and Ubuntu boxes survived the day.

On March 28, the attack surface expanded to include popular third-party applications, which should make for easy pickings on both Ubuntu and Vista. The Vista box took much longer to go down than originally anticipated; it seems SP1 makes these exploits harder, perhaps because of NX support for heap memory, or perhaps the hackers simply didn't prepare on SP1. But in the end, it went down through a new Flash Player vulnerability, which the hacker describes as cross-platform. The Ubuntu machine was the only one left standing. Perhaps the attackers didn't have time to try the Flash Player on Linux.

One more point about CanSecWest that should be made: It's just possible that the market for vulnerabilities, especially for preauthentication vulnerabilities, has higher prices than the CanSecWest show. Why blow a great vulnerability for $20,000 when you can get $50,000 elsewhere?

Even so, Apple doesn't tend to do well at these hacker events. It has a history of getting embarrassed. And back in the day of the Month of Whatever Bugs, the Month of Apple Bugs was probably the best of them. Put a Mac up against a serious attack, and it drops like a stone.

In owning the Mac, it's likely that Miller used this recently revealed vulnerability in the Safari Webkit to exploit the machine, but nobody's talking. Safari is prone to a remote code-execution vulnerability because it fails to adequately handle regular expressions with large, nested repetition counts. Inaccurate compilation lengths are calculated, and an overflow results.