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🔑 Key Takeaways

  1. Curiosity can lead to unexpected career paths, as demonstrated by HD Moore's journey from exploring ways to connect to computers in the 90s to becoming an internet security expert. Stay curious and explore new ideas.
  2. In the 90s, Phrack Chat and hacker magazines served as key resources for learning hacking skills, leading to the recruitment of talented hackers for DoD contractors and the birth of startups like Digital Defense. However, finding exploits remained a challenge, with outdated exploits from hacker websites serving as a last resort.
  3. Metasploit simplifies the process of building an exploit toolkit by providing a single application with trusted and uninfected exploits. It allows users to choose which exploit to use and input parameters to launch it on the target. With lego-like payload options, payloads can be easily assembled and injected into a system after penetration. The tool constantly updates to include new vulnerabilities.
  4. When used properly, tools like Metasploit can help companies identify vulnerabilities and improve their security, but it's important to approach their use with caution and consideration for potential liability issues.
  5. The creation and distribution of hacking tools such as Metasploit require careful consideration of the ethical and legal implications. While they are crucial for penetration testing, understand the potential risks and consequences before designing or sharing them.
  6. Despite the potential risks, reporting unknown vulnerabilities to the relevant teams for fixing and contributing to the community is essential for creating a safe and secure digital environment. Determination and motivation are necessary to overcome pressure to bury vulnerabilities.
  7. HD Moore countered a DDoS attack on his website by hijacking the attackers' botnet. The hacktivist community's infighting and attacks can result in years of trolling and chaos.
  8. While it's important to report vulnerabilities, some may encounter resistance from security teams or companies. Pushing through and persisting in reporting can lead to important discoveries and successes.
  9. Public disclosure of vulnerabilities is necessary to test and improve security measures, and companies should prioritize transparency and collaboration with researchers to ensure their products are secure.
  10. Microsoft's security issues led to the rise of Metasploit and the realization that companies can't control what people do with their product vulnerabilities. Accepting the importance of independent security research, Microsoft improved their security measures.
  11. When disclosing vulnerabilities, privately informing software makers and allowing time for fixing is safer than publishing publicly. A 90-day policy can be effective in ensuring quick fixes and discouraging criminal use of vulnerabilities.
  12. Meterpreter is a powerful tool that can grant full access to a target computer, but its capabilities can also be abused, making it a highly sophisticated and dangerous malware. Vendors face challenges in detecting and protecting against Meterpreter's advanced communication channels and mechanisms.
  13. Always prioritize ethical use of tools to avoid legal consequences. Document after-exploit scenarios and create post-cleanup modules to remove traces. Avoid persistent infections and use the tool to demonstrate security impact, not for committing crimes.
  14. While open-source software makers claim no responsibility for misuse, prosecutors may target individuals regardless of intent. To avoid trouble, stay vigilant and avoid software that could be perceived as a tempting target.
  15. Metasploit, once viewed as a controversial security tool, has become a vital part of the pen testing community. Learning how to effectively use it and contributing to open-source projects can lead to great career opportunities in the field.
  16. Commercializing open-source tools can be profitable while simultaneously promoting accessibility and legal vulnerability disclosure.
  17. Using open-source cybersecurity tools like Metasploit can help protect your systems from vulnerabilities. However, the Wassenaar Agreement makes it difficult, so Rapid7 worked with lobbyists to differentiate between malicious and helpful tools, ensuring Metasploit remained open-source and free.
  18. Writing successful heap exploits on modern ARM platforms requires deep knowledge, months or years of specialization, and comfort working in the unknown. Facing the constant darkness of technology is essential to find vulnerabilities.
  19. Believe in your vision and persevere through tough times to bring about real change, just like HD did with Metasploit, which paved the way for companies like Microsoft and Google to change their approach to handling vulnerabilities. Rumble Network Discovery can also help companies identify multi-owned systems and breaches quickly and effectively.

📝 Podcast Summary

The Robot Arrest Incident and HD Moore's Path to Internet Security

The 1982 incident of a robot being arrested by the police was caused by two teenage boys remotely controlling it to hand out business cards. This incident caused a commotion, leading to the police disconnecting its power source and taking it into custody. Back then, the concept of a robot handing out business cards was a novel idea, but today, it would hardly be noticed. The lack of websites in the 90s caused people to search for ways to connect to computers by dialing numbers, which led to HD Moore's curiosity in finding computers available to outsiders for connection. This curiosity eventually sparked his interest in security research, which led him to become an internet security expert.

How Phrack Chat and Hacker Magazines Transformed the Game of Hacking and Pen Testing in the 90s

Phrack chat channel and hacker magazines like Phrack served as significant resources for learning hacking skills in the 90s. HD, a high school student, got recruited through Phrack for a job with a DoD contractor building offensive tooling for red teams inside the Air Force. Later, HD co-founded the startup Digital Defense to provide security assessments. However, back in the late 90s, exploits were hard to come by, making it challenging for pen testers to demonstrate to the clients that their systems were vulnerable. The pen testers needed to exploit the system to prove what could go wrong if the clients don't update and act like an adversary would. Finding exploits was a hard part, but some hacker websites would have outdated exploits that could be downloaded.

What is Metasploit and How Does it Simplify Exploit Toolkits?

Metasploit, developed by HD Moore, is an exploit toolkit used for security assessments that provides a basic collection of vulnerabilities. It allows users to pick and choose which exploit to use and input parameters to launch it on the target. Prior to Metasploit, gathering exploits was not easy and building an exploit toolkit in-house was the only option. Metasploit made this process easier by providing a single application with loads of trusted and uninfected exploits. Metasploit 2 simplified the process of assembling an exploit by introducing lego-like payload options. Payloads are actions that are taken after penetrating a system and are injected into the computer via the exploit. The tool is constantly updated to include new vulnerabilities.

Understanding the role of Metasploit in network security and the potential liability issues.

Metasploit is a modular tool that makes hacking easier. It allows the user to pick the exploit, pick the payload, and then choose the target. The tool's primary advantage is the ability to randomize its parts to evade antivirus software. This is because securing a network needs to be multilayered, and antivirus should only be used as a last layer of defense in case everything else fails. However, understandably, some companies are wary of exploiting tools like Metasploit due to the potential liability issues. Though these tools can be dangerous, they have an important role in penetration testing and helping companies secure their networks by identifying possible vulnerabilities.

Creating and distributing hacking tools is a double-edged sword. Penetration testers need attack tools to assess a company's vulnerabilities, but designing and sharing these tools can come with legal and ethical risks. The decision to release Metasploit as a free, open-source tool was met with resistance and even hostility from the cybersecurity community. However, this tool revolutionized the way penetration testers worked and made their job much easier. Metasploit continues to be a valuable resource today, but its creation and distribution highlight the complex ethical and legal considerations that come with designing and using hacking tools.

The Importance of Vulnerability Reporting Despite the Risks and Backlash

Publishing exploits can lead to personal attacks, DDoS attacks on the employer's website, identity theft, and more. Despite the backlash, it's important to report unknown vulnerabilities to the relevant teams for fixing. Having a tool like Metasploit can help in creating exploits from vulnerabilities and contributing them to the community. However, there will always be pressure from various sources, including security vendors and business partners, to bury vulnerabilities and prevent their publication. It takes determination and motivation to continue working on such projects in the face of cancel culture and pressure from various sources, but it is crucial to ensure a safe and secure digital environment for all.

HD Moore Hacks Back Against Black Hat Hackers

HD Moore was targeted by black hat hackers who were angry over a vulnerability he published, resulting in DDoS attacks on HD used his expertise to hijack their botnet by pointing the site to their command and control servers, essentially flooding their own servers. They lost their botnet and eventually contacted HD to plead for its return. He felt like an outsider in all the groups he associated with, including the Phrack channel, the DoD and his professional relationships. The hacktivist community is known for infighting and attacking each other's websites. However, HD did not see his attacks as friendly and they led to years of trolling and chaos.

Overcoming Resistance to Reporting Vulnerabilities

Hackers go to great lengths to find unknown vulnerabilities in software. While it's important to report these vulnerabilities to the vendor, some individuals have a history of difficult interactions with security teams. For example, reporting bugs to Microsoft as a teenager resulted in a series of strange interactions with the nascent security team. Later on, while working for a Microsoft partner, the company did not like having vulnerabilities reported and put pressure on coworkers and the CEO to get rid of the hacker. This experience caused the hacker to develop a chip on their shoulder and drove them to push even harder. The ultimate result was discovering a vulnerability in a fully-patched Windows computer during a Capture the Flag challenge.

The evolution of Microsoft's approach to vulnerability disclosure

Microsoft used to hide vulnerabilities and pressurized the researchers to not disclose them. But with the priority of security as the business, they started the Trustworthy Computing Group in 2002. The vendors used to sit on vulnerabilities for years without disclosing them to the public. HD found a vulnerability that was causing issues with the conference and Microsoft was pressurizing him not to disclose it publicly. Later, someone found the same bug and reported it to Microsoft, after which they fixed it. HD and his friends found 600-700 vulnerabilities in Microsoft's Internet Explorer, but the vendors were not moving on it. The public disclosure of a vulnerability helps in testing your mitigations, controls, and detection to work the way they're supposed to.

The Importance of Independent Security Research and Corporate Responsibility for Product Vulnerabilities

Microsoft's security issues with ActiveX and Internet Explorer caused them to offer jobs to vulnerability researchers and improve their bug handling process. This led to the rise of Metasploit as a tool for pen testers and the realization that companies cannot control what people do with bugs found in their products. HD, a well-known vulnerability researcher, was offered a job by Microsoft but declined due to concerns about the company's motives. Microsoft eventually invited outside researchers to their internal conference and started to improve their security measures. The story highlights the importance of independent security research and the need for companies to take responsibility for the vulnerabilities in their products.

Why Responsible Disclosure is Key for Cybersecurity

When it comes to disclosing vulnerabilities, responsible disclosure is the best approach. Though faster, publishing a vulnerability publicly on the internet can put a lot of people at risk, allowing criminals to use it before it gets fixed. It's better to privately inform the software makers and give them time to fix it. If they fail to fix it, a third party like US-CERT can be involved to reduce pressure on individual researchers and ensure the vulnerability is fixed. Some groups like Google and Trend Micro adopt a 90-day policy where the vendor gets 90 days to fix a flaw before it becomes public. By playing this hardball, vendors act quicker, and the product will be fixed.

The Power and Risks of Metasploit's Meterpreter Payload

Metasploit's Meterpreter payload provides the user with full access to the target computer, including installing a keylogger, capturing screenshots, turning on the mic and webcam, and taking over the VNC desktop-sharing service, making it a powerful tool in the exploitation process. However, such features can easily be abused and cause immense damage. The payload side of the exploitation process has become more complicated and powerful, making it difficult for vendors to detect and protect against. The level of access Meterpreter provides allowed for the building of interesting use cases and demonstrated the full impact of an exploit. Meterpreter's capabilities have also led to its classification as its own malware due to its advanced communication channels and contact mechanisms.

Ethical Use of Metasploit Tool

The Metasploit team focused on the ethical use of their tool and drew a line where they would leave the customer afterwards. They always documented the after-exploit scenario and created post-cleanup modules to remove the trace of whatever their tool did. Their goal was not to persistently infect machines, but rather to demonstrate the security impact of a failed security control or a missing patch. Metasploit became a useful and professional tool, but its effectiveness also attracted cyber criminals who committed crimes with it. The tool's author was proved guilty for knowingly giving it to criminals to commit crimes. Therefore, even if a tool is useful, its ethical use should be the top priority to avoid legal consequences.

The responsibility of the software maker is a critical issue in cases where hacking tools are used for criminal activities. However, open-source software makers like HD claim that they cannot be held accountable for what someone else does with their tool. While intent matters, prosecutors are likely to go after someone they believe is a bad actor, especially in the US where Computer Fraud and Abuse Act doesn't care about intent. To stay out of trouble, it's better not to be a tempting target, especially when the law is vague. However, it's surprising that softwares and hacking tutorials come with a disclaimer, warning users not to use it for illegitimate purposes.

From Controversy to Career Launchpad: The Story of Metasploit

Metasploit was created as a security tool for security testing. The creators did not add a warning because they assumed that people who downloaded it knew what they were getting into. While Metasploit received a lot of criticism from the black hat community and vendors, the law was not mad at it. However, the creators had to keep the project visible and noisy to avoid any legal trouble. Upcoming pen testers should learn how to use Metasploit as it has become a de facto tool used by security professionals and is even taught in schools. Contributing to open-source projects such as Metasploit can launch a career in this field. HD Moore was able to turn Metasploit from a hated tool to a widely adopted and invaluable tool for the pen test community.

The benefits of commercializing open-source tools without compromising on their open-source nature.

Acquiring an open-source tool to commercialize it while keeping it open-source can be a great opportunity. Rapid7 acquired Metasploit and built a pro version of the tool to sell, which allowed the team to pay their own bills within twelve months. Additionally, Rapid7 became a corporate shield for all the drama related to vulnerability research and exploit sharing, hiring lawyers and lobbyists to protect legal front and educate people about the importance of vulnerability disclosure. Criminalizing exploit sharing would prevent defenders from learning and increase the possibility of vulnerabilities being exploited. Therefore, while it's important to regulate vulnerability disclosure, it's equally crucial to ensure that it's legal and accessible for legitimate reasons.

Protecting Vulnerability Research with Open-Source Tools

It is important to test your systems with cyber security tools to understand their effectiveness. The Wassenaar Agreement, an international arms treaty, classified cyber security tools as weapons, making it difficult for vulnerability research to be protected. Rapid7 worked with lobbyists to differentiate open-source tools like Metasploit from malicious and targeted cyber security tools. Metasploit continued to be open-source and free under Rapid7, with continual efforts to improve the tool and get more exploits into it. Creating exploits is a difficult and time-consuming task that requires weeks of work just to identify the bug, and even longer to make the exploit reliable.

Working on Fiddly Heap Exploits Requires Specialized Skills and Knowledge

To work on fiddly heap exploits, one needs a specialized and deep set of skills to get the heap in the right state to build an exploit. Modern exploits, especially on ARM platforms, require a lot of effort, time, and deep knowledge. Specialization and months or years of looking into the software stack is required to write good exploits. It's difficult to find vulnerabilities and zero-days even if one knows they exist. To deal with technology, one should be comfortable with working in the dark, in areas of unknowns. Though it's scary and frustrating to try things that may fail, the more comfortable one gets in unknown territories, the better they'll be to face the darkness, which is constant.

The Importance of Perseverance in Cybersecurity and Network Discovery

Rumble Network Discovery helps companies in finding every single thing connected to their network environment or cloud with no network impact. It can identify multi-owned systems breaching different networks which is done unauthenticated and quickly. HD struggled to make Metasploit and faced constant attacks for publishing exploits, but persevered through it all due to his belief that what he was doing is right and the world was wrong. His vision turned out to be right as companies like Microsoft and Google changed the way they handle bugs and vulnerabilities. The struggle highlights the importance of putting beliefs and vision ahead of criticism and persevering through tough times to bring about real change.