The iPhone has been around for nearly 17 years. While the device has evolved significantly since its launch, one thing has remained constant: Apple’s tightly controlled ecosystem.
Fighting jailbreaking. Apple has gone to great lengths to prevent users from modifying their iPhones. But even with the first-generation device, some pushed back, offering an alternative: jailbreaking.
Jailbreaking exploits vulnerabilities to bypass Apple’s restrictions, allowing users to unlock features otherwise unavailable. However, it comes with security risks.
The Allegra way. One of the most notable hackers in this space was Nicholas Allegra.
Known online as “Comex,” the 18-year-old released the first widely available jailbreak for the iPhone 4 in 2010. He discovered a vulnerability in Safari’s library that let users jailbreak their devices directly from the browser.
Pushing the limits. Comex continued refining his ability to crack Apple’s security. In 2011, he released JailbreakMe 3.0, which worked across multiple iOS devices, including the iPad 2. By then, the hacking community believed he was “years ahead” of others in iOS security research.
Apple hired him. That same year, everything changed. Apple, the very company he had challenged, brought him on as a remote intern. However, his time at Apple didn’t last long.
Fired over an email. After nearly a year, Allegra announced on Twitter (now X) in 2012 that he was no longer with Apple. He later clarified that the reason was simple: He had “forgotten to respond to an email.”
The email in question was Apple’s offer to extend his internship for another year. When he didn’t reply, the company terminated his contract. Just like that, the iPhone hacker’s time at Apple was over.
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