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Vulnerabilities / Threats

Apple SSL Vulnerability: 6 Facts

SSL vulnerability that's been patched in iOS -- but not yet for OS X -- lets attackers intercept email and FaceTime communications, plus push malicious software updates.

Apple Mac Pro: 9 Ways It Wows
Apple Mac Pro: 9 Ways It Wows
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The SSL vulnerability that affects iOS devices, as well as desktops and laptops that run the Apple OS X operating system, is easy to exploit and likely already being actively targeted by attackers.

So said New Zealand security researcher Aldo Cortesi, who reported Tuesday that he successfully adapted a free man-in-the-middle proxy tool called mitmproxy -- which is designed to intercept, modify, and replay HTTP and HTTP traffic -- to exploit the SSL flaw.

"I've confirmed full transparent interception of HTTPS traffic on both iOS (prior to 7.0.6) and OS X Mavericks. Nearly all encrypted traffic, including usernames, passwords, and even Apple app updates can be captured," according to a blog post from Cortesi, who promised to not release his SSL-attack tweaks for mitmproxy until after Apple releases an OS X patch.

"It's difficult to over-state the seriousness of this issue. With a tool like mitmproxy in the right position, an attacker can intercept, view, and modify nearly all sensitive traffic. This extends to the software update mechanism itself, which uses HTTPS for deployment," Cortesi said. "It's safe to assume that this is now being exploited in the wild. Of course, intelligence agencies have no doubt been on top of this for some time."

[Are you willing to trade personal property rights for security? See Kill Switches: Phones Just The Start.]

With the above in mind, here are six crucial issues facing Apple iOS and OS X users.

1. OS X Mavericks hasn't been patched.
Apple issued iOS updates Friday to patch the flaw -- known as CVE-2014-1266 -- in the form of iOS versions 7.0.6 and 6.1.6. Those updates work on the iPhone 4 (and newer devices), iPod Touch (5th generation), and iPad 2 and newer devices. Apple has also confirmed that the SSL flaw affects OS X. "We are aware of this issue and already have a software fix that will be released very soon," Apple spokeswoman Trudy Muller told Reuters Saturday.

2. Flaw facilitates man-in-the-middle attacks.
Crowdstrike senior engineer Alex Radocea said in a blog post that the vulnerability stems from "a flaw in authentication logic on iOS and OS X platforms" that would allow an attacker -- who's connected to the same wired or wireless network as their target -- to bypass SSL/TLS verification routines. "This enables an adversary to masquerade as coming from a trusted remote endpoint -- such as your favorite webmail provider -- and perform full interception of encrypted traffic between you and the destination server, as well as give them a capability to modify the data in flight."

"This sort of subtle bug deep in the code is a nightmare. I believe that it's just a mistake and I feel very bad for whoever might have slipped in an editor and created it," said Google engineer Adam Langley in a blog post.

(Image credit: Apple)
(Image credit: Apple)

3. Attackers could target email, FaceTime, location tracking.
According to a tweet from independent privacy researcher Ashkan Soltani, vulnerable Apple OS X applications and processes include Calendar, FaceTime, Keynote, Mail, Twitter, iBooks, Software Update, and ApplePushService. In other words, an attacker who can exploit the vulnerability would be able to intercept not just a target's email, but also calendar information and videoconferencing sessions. A more sophisticated attacker -- say, an intelligence agency -- might also abuse the Software Update process to push malicious updates to a target.

According to Cortesi, the flaw would allow iCloud data, including KeyChain enrollment, as well as Find My Mac updates -- which broadcast a user's location -- and Twitter certificates to be intercepted.

4. Who filed the anonymous bug report?
News of the Apple flaw sparked questions about whether one or more intelligence agencies knew about it or possibly even reported it to Apple. "One of the fun bits about Apple's recent set security updates is the uncredited: CVE-2014-1266. Why no thank you? Who discovered the issue?" tweeted Sean Sullivan, security advisor at F-Secure Labs.

"Which agency is responsible for protecting comms, wont take credit, & would find a bug deep inside a crypto handshake?" responded the zero-day vulnerability broker known as the GrugQ.

5. Are enterprise users at less risk?
For which versions of OS X does Apple plan to issue an SSL security fix? An Apple spokeswoman didn't immediately respond to an emailed question. But according to Google's Langley, "it looks like the bug was introduced in 10.9 for OS X," meaning that anyone who has yet to upgrade to Mavericks may be protected against this particular flaw.

That means that the majority of enterprises that use Macs may be safe from related attacks. Security firm Sophos reported in January that 77 days after Apple released Mavericks, 55% of consumers who use its free Mac antivirus product had adopted the new operating system, but only 18% of enterprise users had upgraded.

6. Unpatched: iOS background monitoring flaw.
Apple has yet to patch the SSL flaw for OS X users, but it may be preparing another security update for iOS 7 and iOS 6 users. Security firm FireEye reported Monday that it had discovered a flaw that allows an attacker to conduct background monitoring of non-jailbroken devices running those versions of Apple's mobile operating system. Attackers could use this monitoring "to reconstruct every character the victim inputs," according to a blog post from FireEye, which said it's working with Apple to help fix the problem.

IT is turbocharging BYOD, but mobile security practices lag behind the growing risk. Also in the Mobile Security issue of InformationWeek: These seven factors are shaping the future of identity as we transition to a digital world. (Free registration required.)

Mathew Schwartz served as the InformationWeek information security reporter from 2010 until mid-2014. View Full Bio

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User Rank: Apprentice
2/28/2014 | 10:47:09 PM
Patch Time
When things like this arise, I think most about people running the older versions of their operating system. Apple took longer than expected to push out the OSX patch, but they did in the end push it out fairly quickly. The iOS patches I thought were done very quickly once the new had broken. I wonder then about similar types of Windows problems and whether Microsoft would, for example, patch Windows XP, which is still in use on a depressing large number of computers.

I heard reports saying that this was a failure in their software development process. I guess that's true, as it means they did not fully test that element after making changes. Once passed through, it seems unlikely that it woudl be caught by most automated methods.
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