Unpatched stealthy iOS MDM hack spells ruin for Apple tech enterprises

Clicking 'OK' to ordinary and expected phishing prompt enough for complete iPhone compromise

Black Hat Asia Enterprises the world over are at risk from a seamless new attack that allows the latest Apple devices to be quietly compromised in what researchers say requires a total overhaul of Cupertino's enterprise provisioning architecture for mobile device management.

The unpatched hack – dubbed SideStepper and crafted by Israel-based Check Point hackers Ohad Bobrov and Avi Bashan – begins with a near-perfect phishing attack targeted at staff, and ends with complete compromise of fully updated iOS devices running version 9.2.

It takes advantage of Apple's newly streamlined enterprise provisioning architecture, which allows tech shops to install non-App Store applications on staff handsets.

Mobile device management of Apple devices is a system used by almost all Fortune 100 companies and scores more enterprises. Almost all are at risk of the attack, the pair told The Register.

Apple's upgrade means attackers need only send an SMS – to trick staff into accepting a legitimate-looking request to install a configuration file – for attackers to have remote man-in-the-middle access. From there, attackers can install applications that will quietly eviscerate Apple devices.

The attack demonstrated to The Register by Bobrov and Bashan ahead of their presentation at BlackHat Asia today generates a pop-up on staff handsets that would appear typical of those requests generated by mobile device management platforms.

Apple has been contacted for comment. However, the pair say they informed the tech giant of their research, and Apple labeled it "a feature, not a bug."

The pair say the attack is cleaner and more deadly than any that have come before, and is explicitly thanks to Apple borking its enterprise provisioning service.

"We found a way to do a man-in-the-middle attack on an iOS mobile device and replace an original command such as 'query device' with one to install a malicious enterprise certificate application," Bobrov says.

"That pretty much seamlessly installs a malicious application on the device, and then game over."

Bashan says a configuration profile sent to devices and accepted by users will install routing commands and root certificates, which combined let attackers route and decrypt handset traffic to their servers.

"Once staff open the malicious app, sensitive data like contacts, emails, screenshots can be sent to a server so that personal and enterprise data is compromised," Bashan says.

"Apple tried to solve the problem but actually made it worse, because now it is even easier to infect a mobile device."

Cupertino indeed made it easier for enterprise provisioning, which has been a target of black and white hats since the FinFisher government mobile malware was identified in 2013. Following that revelation, jailbreakers Pangu and white hats behind the Masque attack have targeted the enterprise provisioning vector. Last year alone, Wire Lurker, Hacking Team, and YiSpecter surfaced to pwn the latest iOS devices using the channel.

The phishing configuration file bait resembles a legitimate prompt that is a common sight for staff using handsets controlled by mobile device management systems. Attackers can even mark the phishing installation prompt to continually pop up until users click accept.

Asked what Apple can do to remediate the problem, Bobrov and Bashan say little short of an architectural overhaul will fix the attack vector; patching will not help, they say. Moreover, any significant fix could disrupt businesses running existing mobile device management deployments for Apple devices.

There is also little a typical system administrator can do to detect a handset compromised by the attack. Eagle-eyed staff could report a newly-installed application to IT, foiling the hack, but further attack research makes this scenario even more unlikely.

Separate research by MetaIntell architect Chilik Tamir also showcased at the Singapore hacking conference demonstrates how attackers can install a malicious application that not only looks like a legitimate app, but when tapped, calls and launches the original expected app after it pwns the handsets.

Combined, the two tactics spell trouble for enterprises and opportunity for ambitious attackers.

Bobrov and Bashan are already working on further iOS vulnerability and exploitation research. They also have Android in their sights.

"We love mobile," Bobrov says. "Android as well." ®

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