In April 2007, when Apple's “I'm a Mac” ads were telling people that Macs can't get hacked, security researcher Dragos Ruiu decided to put the idea to the test – in front of a room full of security researchers, no less. He bought two MacBook Pros and put them on the floor of the CanSecWest conference in Vancouver, which he organized. The challenge had a catchy name, Pwn2Own: If you pwn a computer, you own it.

To Ruiu, it was more than a game. He wanted to make a “political point” that the commercials were misleading and Apple should take security seriously.

“Apple has had an on-again, off-again relationship with researchers. Sometimes they love hackers, sometimes they want to pretend hackers don't exist,” Ruiu tells Dark Reading. “This is one of those times when their marketing department used to run their security team.”

Back then, most companies also treated security researchers poorly. If someone found a flaw and reported it, they would often be threatened with lawyers. Part of Pwn2Own's merit is that it helped change that, “normalizing the concept of reporting bugs,” says Dustin Childs, communications manager for Trend Micro's Zero Day Initiative program, who now runs the event.

Throughout the years, the Pwn2Own competition has attracted high-profile researchers, including Dino Dai Zovi, Charlie Miller, George Hotz, Vincenzo Iozzo, Dion Blazakis, Ralf-Philipp Weinmann, and Jung Hoon Lee (aka Lokihardt). They’ve poked at everything, from Macs to phones, to IoT devices, industrial control systems, and even cars.

“It's a demonstration of some of the most advanced exploitation techniques that exist in the industry, at any given point in time,” says Brian Gorenc, senior director of vulnerability research at Trend Micro Gorenc. Demonstrations like these actually change how the industry looks at security.

Researchers’ efforts are well rewarded, too. Last year alone, cash prizes at Pwn2Own –

one of the highest-paying hacking competitions in the world – exceeded $2.5 million in total during multiple events.

This year’s contest, which starts today, marks its 15th anniversary and includes six categories: virtualization, Web browser, enterprise applications, server, local escalation of privilege, enterprise communications, and automotive. Whoever earns the most points will be crowned Master of Pwn, which will guarantee them “a killer trophy and a pretty snazzy jacket to boot.”

Early Pwn2Own Wins
But let’s start with a recap of the first day of the 2007 CanSecWest conference, when two MacBook Pros with the latest security updates were in the spotlight, waiting to be hacked. A few researchers tried their luck, but the computers survived.

Then, security expert Shane Macaulay, who was in attendance, called former co-worker Dino Dai Zovi, based in New York, and asked him if he wanted to participate.

“I said, OK, cool, let me sit down and take a look and see what I can find,” Dai Zovi said in an interview a week after the conference. It took him five hours to detect a bug and another four to write the exploit. At 3 a.m., he called Macaulay, telling him they might actually win.

Dai Zovi found a bug in a QuickTime library loadable through a Java applet. An attacker could exploit it through any browser on Mac OS X that supports Java applets, such as Safari and Firefox. He sent his exploit to Macaulay, who put it on a website and emailed its URL to the organizers of the challenge. Once they loaded the malicious Web page, Macauley obtained a remote shell that granted him control of the laptop. The duo pwned the machine, earning them a 15-inch MacBook (which Macaulay kept since Dai Zovi had recently bought himself a laptop) and a $10,000 cash prize, courtesy of the Zero Day Initiative.

Dai Zovi says winning the first Pwn2Own event changed his life. “It was a massive benefit to my career and really put it on a different and better trajectory,” he says. “At the time, I had been writing exploits quietly as a personal hobby for almost a decade but was not at all known for it.”

The reputation he gained led him to consulting projects on iOS security and writing a book with another Pwn2Own rockstar, Charlie Miller, “The Mac Hacker's Handbook,” followed by “iOS Hacker's Handbook.”

Miller found himself in the spotlight the following year when he wrote an exploit for Safari with colleagues Jake Honoroff and Mark Daniel. “It might be because I'm biased about the things I'm good at, but [Safari is] the easiest browser [to hack],” Miller said in an interview after the competition.

Beyond Apple
But Pwn2Own wasn’t only about Apple products. During the 2008 event, a Fujitsu U810 laptop running Vista was also attacked with an exploit for Adobe Flash written by Shane Macaulay, Alexander Sotirov, and Derek Callaway.

“In the very beginning, Pwn2Own was very much a browser-focused contest, and over the years, we've expanded the attack surfaces,” Gorenc says. “We've raised the prizes to make it more attractive for people to come in.”

Indeed, by 2015 the total cash prices exceeded $500,000. This month’s event, held in a hybrid format, has up to $600,000 waiting for the hacking of the Tesla Model 3, the largest target in Pwn2Own history.

But it is not only about money. “Pwn2Own was the first competition that focused on demonstrating real, working zero-day exploits against real-world software, whereas before most security competitions were capture-the-flag competitions that focused on “mock” targets and vulnerabilities,” Dai Zovi says. “It really put the focus on what was possible against the software that millions, if not billions, of people use to put a spotlight on how much we needed to improve security.”

When ‘Wow’ Is an Understatement
The Pwn2Own competition has expanded to include software like MS Office, Adobe Reader, and Zoom. It has also tested the security of iPhones and BlackBerrys, and featured attacks targeting SCADA systems and IoT devices.

Some of the hacks were just mind-blowing and “times when 'wow' just isn't enough,” according to an HP Security Research blog post published during the 2015 event. That was when Jung Hoon Lee from South Korea hacked three browsers: Internet Explorer 11 (he found a time-of-check to time-of-use vulnerability), both the stable and beta version of Chrome (he exploited a buffer overflow race condition in the browser), and Safari (he exploited an uninitialized stack pointer in the browser).

Another exciting hack happened in 2017, when a team of researchers from Chinese Internet security company Qihoo 360 broke into VMWare's virtual machine sandbox.

“They fired up a virtual client, a fully patched Windows box. They pulled a fully patched browser and browsed to a Web page. They took their hands off the keyboard and let everything run,” Trend Micro's Childs says. “They combined enough bugs to break out of that [sandbox] and execute code on the underlying hypervisor on VMware Server underneath. And it was astonishing.”

Hacks like these made vendors feel edgy before the competition, and sometimes they would even push updates before an event.

“One year we got to Vancouver only to find out that the version of the BlackBerry deployed in Canada actually patched our bug, so we had to not sleep for two nights straight to fix the exploit,” says security expert Iozzo.

But, he adds, things like that were part of Pwn2Own's cachet. Many hackers who attended these events say they were both intense and fun. In March 2019, team Fluoroacetate, which took its name from a highly toxic substance that can kill bugs, found a severe memory randomization bug in Tesla's Model 3's infotainment system. Team members Richard Zhu and Amat Cama were crowned Masters of Pwn, earning $375,000 and the car.

Humor and jokes complement the stress associated with hacking.

“Last year also, we had someone hack a printer and play AC/DC through the speaker, which was pretty inventive,” Childs says. “We're dealing with a serious subject matter; the impact of these bugs can be tremendous. But at the same time, we try to keep the attitude light for the competitors so that we don't take ourselves too seriously.”

Pwn2Own's Contributions to Bug Hunting
When the first edition of the Pwn2Own competition took place, the concept of hunting bugs was pretty exotic. Most companies were reluctant to talk to security researchers who reported issues, and even vendors who attended Pwn2Own events had mixed feelings about it.

But as the competition gained attention and brought everyone good publicity, companies started to open up. Looking back, security researcher Ruiu says that Pwn2Own partially assumed the role of negotiator, helping hackers get decent pay for their work.

“The manufacturers would love to just say: Have a T-shirt here,” Ruiu says. “But we became advocates for the security developers.”

As security experts and vendors met in the disclosure room to talk about hacks, the mood became less adversarial and more cooperative. The result: Bugs were fixed promptly before being exploited by a malicious entity.

Pwn2Own showed “it was OK for responsible organizations to compensate individual researchers for the hours of work put into their findings,” and led many large software companies to support bug-bounty programs, says Terri Forslof, a threat analyst at Microsoft.

Ruiu agrees, saying that Pwn2Own has helped pave the way for bug-bounty platforms like HackerOne and Bugcrowd, which work as intermediaries between researchers and tech companies. In 2021, HackerOne paid nearly $37 million for more than 66,500 valid bugs; the median earning for a critical bug was about $3,000. Also last year, Google offered bug hunters $8.7 million, while Zoom paid out $1.8 million.

Ruiu's initial goal of getting Apple to take security seriously has also been achieved, at least in part. The Cupertino, Calif., giant is currently offering up to $1 million to security experts for an exploit that results in a zero-click kernel code execution with persistence and kernel PAC bypass.

But although the role bug bounties play is undeniable, related issues remain. They still need to be formalized, says Childs, adding that such projects are not for everyone. “They're not a one-size-fits-all thing,” he says.

Many companies start bug-bounty programs without having a mature response process in place to be able to handle the reports they receive. As Childs puts it, “They get all these bugs, and they don't know what to do with them.” Organizations should have an efficient triage and specific procedures process in place to roll updates to customers, he points out.

“Until you have that basic, fundamental process available, offering a bug-bounty program is actually going to be more harmful than good because you're going to be getting bugs, and you're going to be overwhelmed by that,” Childs says. “And then you begin to have an adversarial relationship with the people who are reporting, even though you ask them to report.”

Hackers also complain. Some say they are underpaid for the bugs they discover, while others argue that their efforts are not always acknowledged in full.

During this week’s Pwn2Own, both Ruiu and ZDI hope to make one more small step in the right direction. “It still continues to change; it evolves continuously,” Ruiu says. “One of our goals is to improve the relationship between vendors and independent researchers.”