Top 5 Most Technically Advanced Hacking Attacks of All Time

Cyberattacks have become ubiquitous as the internet has expanded to touch almost every aspect of commerce and human interaction. Like any sort of crime, cybercrime goes where the victims are. It seems we’re fast becoming desensitized to the bigger implications of major cyber attacks amid the endless litany of reports of people and corporations getting hacked.

Lost in the shuffle of all that crime is the fact that relatively little of it conforms to the Hollywood expectation of what hacking is: a nefarious villain in a reclusive, dark location, lit only by the glow of computer monitors and using their superior coding skills to exploit vulnerabilities in commercial software.

Instead, most hacking is rote—social engineering, like phishing attacks, or canned exploits built into downloadable cracking tools like Metasploit. Most hackers have almost no actual technical skills. They follow instructions or perform the same kind of confidence schemes their kind would have been using even if computers had never been invented.

That makes legitimately challenging technical hacks all the more impressive. The ability to uncover a vulnerability, code an exploit, and deploy it in the unpredictable terrain of the wild internet requires enormous skill, and is something that happens only rarely. As rare as they may be, these are the most dangerous adversaries and events that cybersecurity professionals might ever have to face.

Here’s a look at the top 5 most technically advanced hacking attacks of all time.

  1. Operation Aurora – 2009

    Operation Aurora was an attack launched in 2009 directly at major American corporations, including Google, Dow, and Northrop Grumman by a unit most researchers believe to be operated by the Chinese Government. Certainly the actions of the attackers once they gained entry to Google’s systems supported this conclusion—they immediately attempted to access data stored by the Internet giant belonging to Chinese dissidents, such as the Gmail account of artist and journalist Ai Wei Wei.

    That Google, keeper of so much of the sensitive data of the world, could have been compromised indicates in part how sophisticated the attack was. But like so many other hacking attacks, it started out as a social engineering exploit… spearphishing emails targeting Google staff that were likely to have access to the information the attackers were after.

    From there, though, the technical aspects of the attack escalated. The emails included a link, leading to a malicious website. The site exploited previously unrevealed flaws in Microsoft’s Internet Explorer software that allowed the attackers to gain access to the user’s computer.

    It’s unclear whether the users got in more trouble for clicking on insecure links or for using IE instead of Google’s own Chrome browser, which wasn’t susceptible. The irony is at least as hilarious as it is painful.

  1. Code Red – 2001

    Code Red was one of the great grandaddies of the massively spreading computer worm. Introduced in 2001, it attacked Microsoft Internet Information Server web server software via a buffer overflow. Although Microsoft had identified the vulnerability and issued a patch, many organizations had not applied it by the time attackers developed the exploit – attackers that were still unidentified at the time, but thought to have been working in the Philippines, despite a string in the code reading “Hacked by Chinese!” A real subtle red herring, huh?

    Code Red infected somewhere between 1 million and 2 million computers in 2001, a somewhat surprising number considering the fact that it announced itself brazenly by defacing the content of web pages served up on infected machines. It also attempted to execute a denial of service attack against

    Despite the amateur theatrics, Code Red was coded to run entirely in memory, leaving no files on the server hard drive for virus scanners to easily detect or eradicate.

  1. Heartbleed – 2014

    Most of modern computer and network security rest on a firm foundation of proven modern encryption algorithms. But while the math behind the encryption can be solid, the implementation in coding terms sometimes is not so robust. And in April of 2014, a flaw was found in one of the most widely used cryptographic libraries in the world, OpenSSL.

    OpenSSL use commonly used to implement the Transport Layer Security (TLS) encryption that serves up secure web pages and encrypts e-mail messages for privacy. OpenSSL is available on every popular server operating system and provides the encryption layer for most of the Internet.

    And it had a bug. A buffer overread could occur, allowing attackers to read material from a server that other users believed to be encrypted. Those could include authentication materials or other sensitive data that could allow further access.

    Those attacks resulted in thefts from the Canadian Revenue Agency and Community Health Systems, the second largest for-profit hospital chain in the United States. It’s unclear exactly when the vulnerability was discovered by black-hat hackers or how long they might have been exploiting it.

  1. Conficker – 2008

    Conficker was a combination punch that exploited flaws in Microsoft’s Windows NetBIOS networking service while launching rudimentary brute-force dictionary attacks against weak administrator account passwords. This effective one-two punch allowed it to become the worm to be reckoned with on the Internet in 2008 and 2009.

    The worm infected millions of computers worldwide, becoming the largest botnet infection since 2003.

    Conficker wasn’t the first worm designed to build a botnet and it didn’t use completely innovative infection and management techniques, but it was unusually sophisticated in how it combined existing virus coding and botnet control schemes to become extraordinarily difficult to eradicate. The worm component incorporated self-defense mechanisms to prevent infected machines from easily removing it, including blocking DNS lookups and disabling Windows auto-update.

    It also used a semi-random auto-generating domain name control scheme, that prevented administrators from easily blocking connections to the net controller machines.

    As time passed, it became clear that the virus authors were monitoring the response to the virus and coding in updates and new variants based on how Microsoft and anti-virus organizations were combating the virus.

    Although cybersecurity teams managed to block access to net controllers by the end of 2009, Conficker just won’t die… even as recently as 2015, as many as half a million machines remained infected.

  1. Stuxnet – 2010

    Stuxnet should probably get several top spots on this list, considering the groundbreaking number of technical achievements in the worm. Stuxnet made use of no fewer than four completely unrevealed zero-day exploits in Microsoft’s Windows software, where most exploits would be considered newsworthy if they found only one.

    It was the first ever rootkit designed for use in Programmable Logic Controller (PLC) architecture, and possibly the first exploit used to physically destroy or disable industrial hardware. Even more impressively, one variant of the worm, dubbed Flame, distributed itself by insinuating itself into Microsoft’s official Windows Updates, looking exactly like an official patch.

    Stuxnet also made use of advanced Bluetooth snooping abilities, allowing it to attack devices not even physically connected to computer networks.

    Such sophistication has lead most experts to conclude that Stuxnet was coded by a team working for U.S. and Israeli intelligence, and designed specifically to attack Iran’s nuclear program.

    Ironically, for such sophisticated malware, Stuxnet was only discovered because of a bug that allowed it to inadvertently spread outside the target region of Iran… a lesson in how quickly such tools can get out of hand.

    Such zero-day exploits are often the hallmark of nation-state attacks, and the technical game of such advanced persistent threats will continue to pose a serious challenge to cybersecurity professionals. The importance of an advanced degree in the field is never more clear than when dealing with such complicated attacks.