What the newly released Checkra1n jailbreak means for iDevice security

What the newly released Checkra1n jailbreak means for iDevice security

Enlarge (credit: @Checkra1n)

It has been a week since the release of Checkra1n, the world’s first jailbreak for devices running Apple’s iOS 13. Because jailbreaks are so powerful and by definition disable a host of protections built into the OS, many people have rightly been eyeing Checkra1n—and the Checkm8 exploit it relies on—cautiously. What follows is a list of pros and cons for readers to ponder, with a particular emphasis on security.

The good

First, Checkra1n is extremely reliable and robust, particularly for a tool that’s still in beta mode. It jailbreaks a variety of older iDevices quickly and reliably. It also installs an SSH server and other utilities, a bonus that makes the tool ideal for researchers and hobbyists who want to dig into the internals of their devices.

“I expected it to be a little rougher around the edges for the first release,” Ryan Stortz, an iOS security expert and principal security researcher at the firm Trail of Bits, said in an interview. “It’s really nice to be able to install a new developer beta on your development iPhone and have all your tooling work out of the box. It makes testing Apple's updates much much easier.”

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A host of new security enhancements is coming to iOS and macOS

(credit: Nathan Mattise)

Apple on Monday previewed a variety of security and privacy features it plans to add to macOS and iOS operating systems, including encrypted Facetime group calls, password-management tools, and camera and microphone protections. The company also released a beta version of the upcoming iOS 12 that, according to Motherboard, all but kills off two iPhone unlocking tools used by police forces around the world.

The feature, known as USB Restricted Mode, requires that users unlock their iPhone with a password when connecting to it a USB device. Motherboard said the beta requires a password each time a phone that hasn’t been unlocked in the past hour tries to connect to a device using a Lightning connection. The password requirement largely neutralizes iPhone unlocking tools provided by companies called Cellebrite and GrayShift, which reportedly use USB connectivity to bypass iOS restrictions on the number of incorrect PIN guesses can be entered into an unlocked iPhone. With those limitations removed, police can make an unlimited number of PIN guesses when attempting to unlock a confiscated iPhone.

Previous iOS betas had USB restrictions that required the entering of a password when it hadn’t been unlocked for seven days. Those USB Restricted Modes were later removed before Apple issued final versions of iOS. The restrictions this time around are much more stringent, because police would have no more than 60 minutes between the time they obtain an iPhone and connect it to an unlocking tool. Readers should remember that Apple has previously removed USB Restricted Mode before releasing final versions and may do so again with iOS 12.

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A host of new security enhancements is coming to iOS and macOS

(credit: Nathan Mattise)

Apple on Monday previewed a variety of security and privacy features it plans to add to macOS and iOS operating systems, including encrypted Facetime group calls, password-management tools, and camera and microphone protections. The company also released a beta version of the upcoming iOS 12 that, according to Motherboard, all but kills off two iPhone unlocking tools used by police forces around the world.

The feature, known as USB Restricted Mode, requires that users unlock their iPhone with a password when connecting to it a USB device. Motherboard said the beta requires a password each time a phone that hasn’t been unlocked in the past hour tries to connect to a device using a Lightning connection. The password requirement largely neutralizes iPhone unlocking tools provided by companies called Cellebrite and GrayShift, which reportedly use USB connectivity to bypass iOS restrictions on the number of incorrect PIN guesses can be entered into an unlocked iPhone. With those limitations removed, police can make an unlimited number of PIN guesses when attempting to unlock a confiscated iPhone.

Previous iOS betas had USB restrictions that required the entering of a password when it hadn’t been unlocked for seven days. Those USB Restricted Modes were later removed before Apple issued final versions of iOS. The restrictions this time around are much more stringent, because police would have no more than 60 minutes between the time they obtain an iPhone and connect it to an unlocking tool. Readers should remember that Apple has previously removed USB Restricted Mode before releasing final versions and may do so again with iOS 12.

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iPhone exploit bounty surges to an eye-popping $1.5 million

Enlarge (credit: Antoine Taveneaux)

A controversial broker of security exploits is offering $1.5 million (£1.2 million) for attacks that work against fully patched iPhones and iPads, a bounty that's triple the size of its previous one.

Zerodium also doubled, to $200,000, the amount it will pay for attacks that exploit previously unknown vulnerabilities in Google's competing Android operating system, and the group raised the amount for so-called zeroday exploits in Adobe's Flash media player to $80,000 from $50,000. After buying the working exploits, the company then sells them to government entities, which use them to spy on suspected criminals, terrorists, enemies, and other targets.

Last year, Zerodium offered $1 million for iOS exploits, up to a total of $3 million. It dropped the price to $500,000 after receiving and paying for three qualifying submissions. On Thursday, Zerodium founder Chaouki Bekrar said the higher prices are a response to improvements the software makers—Apple and Google in particular—have devised that make their wares considerably harder to compromise.

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