Security Boulevard

In this second post of a five-part series, I provide advice on how to best utilize the PEN-200 course material for a successful career in ethical hacking.

Disclaimer:

All opinions expressed in this article are solely my own. I have reviewed the content to ensure compliance with OffSec’s copyright policies and agreements. I have not been sponsored or incentivized in any way to recommend or oppose any resources mentioned in this article.

Introduction

In my previous post in this series, I discussed practical steps students could take before enrolling in the PEN-200 to get the most value out of the pursuit for the Offensive Security Certified Professional (OSCP) certification. The next step is to discuss what to do while reading the official course material.

PEN-200: Penetration Testing Certification with Kali Linux | OffSec

During the Course

“One hour per day of study in your chosen field is all it takes. One hour per day of study will put you at the top of your field within three years. Within five years, you’ll be a national authority. In seven years, you can be one of the best people in the world at what you do.” — Earl Nightingale

The PEN-200 course is composed of 28 distinct modules covering fundamental penetration testing concepts. In this post, I discuss my advice for students starting the course. My three main arguments are:

1. Use the note-taking process and exercises in PEN-200 as a chance to build confidence with tools and platforms relevant to offensive security roles
2. Not all PEN-200 techniques are practical for real-world assessments — some require adaptation to evade defenses while others risk service disruption, credential exposure, and more; understanding these nuances will make you a more effective and responsible professional
3. PEN-200’s curated references to blogs, proof of concepts (PoCs), and whitepapers provide not only valuable learning but also insight into key industry contributors, which can give you an edge in job hunting and networking

Use Job-Relevant Tools and Platforms to Write Your Notes

The OSCP certification is primarily geared towards beginner-level security professionals, so it’s fair to assume that most students have limited experience with the tools that offensive security consultants commonly use. The PEN-200 course provides a valuable opportunity for OSCP candidates to gain exposure to these tools and build their proficiency before entering the field.

To clarify, this section is not about the “hacking tools” you will inevitably use to identify and exploit vulnerabilities — PEN-200 provides ample guidance on those. My advice focuses on tools that are tangential to offensive tasks but still widely used in cybersecurity roles.

The PEN-200 course is designed to be completed using Kali Linux, a Debian-based distribution pre-installed with many of the most popular tools for offensive security testing. While Kali is convenient for quickly deploying a Linux virtual machine (VM) with a broad toolkit, you shouldn’t feel restricted to using it for professional development. Experiment with other Linux distributions (e.g., Parrot OS, BackBox Linux, BlackArch) and even Windows-based distributions (e.g., CommandoVM, FLARE-VM) while improving your proficiency with virtualization software like VMWare or VirtualBox.

Kali Linux | Penetration Testing and Ethical Hacking Linux Distribution

Although it is more commonly associated with software development, git — the popular version control system — is a valuable asset to offensive security consultants. Deploying your PEN-200 notes to a git repository offers a great opportunity to improve your fluency with fundamental operations like commit, pull, push, merge, and more. The biggest hurdle to mastering git is often the concept of “branching”: the process of diverging from the master branch (often called master or main , depending on your platform), making independent changes, then later merging those changes back into the main branch. Fortunately, there are many excellent online tutorials to help with this.

Learn Git Branching

If you choose to use git for your notes, consider hosting them in a private repository on GitHub or GitLab. Both platforms are based on git but offer additional features such as access control, repository templates, Markdown support, and more. Personally, I prefer GitLab for storing my notes due to its granular visibility controls, but GitHub is undeniably the most popular option and the one you’re most likely to encounter in a cybersecurity role. Whichever platform you choose, make absolutely sure it’s locked down and only you can access it. Copyright infringements of OffSec’s proprietary course materials — even accidental ones — can result in punitive responses from OffSec.

Now that you’ve chosen where to host your notes, it’s time to start writing them! The three most popular command-line text editors are Vim, Emacs, and nano. Of these, nano is the most beginner-friendly and an excellent starting point. Both Vim and Emacs are feature-rich and highly customizable, but have a high learning curve. If productivity and modularity are values you prioritize, it pays to start learning one (or both) early. The debate over which is superior is so enduring that it even has its own Wikipedia article.

Of the two, I only have experience with Vim, so it’s the only one I can recommend. Its commands can be confusing at times, but it’s a huge productivity booster in the long-run. If you decide to go down the Vim rabbit hole, I recommend starting with Vi, Vim’s precursor. Vi supports fewer commands, but is more likely to be encountered on older Linux distributions, so you won’t be caught off guard when your favorite Vim commands aren’t working. Once you’ve got the hang of Vi and are ready to graduate to Vim mastery, consider using the online tutorial/game VIM Adventures to hone your skills.

Learn VIM while playing a game - VIM Adventures

Command-line text editors can be fun, but they’re not for everyone. If that’s you, I highly recommend Obsidian as your note-taking application. As I discussed in my last blog post, Obsidian is an extremely popular graphical text editor packed with useful features. In 2021, an employee of the cybersecurity consulting firm TrustedSec published a blog post detailing how they incorporated Obsidian into their internal tradecraft documentation. While this setup isn’t a one-to-one equivalent of an online course, the features showcased in the article — especially the usage of the Obsidian-Git community plugin — are particularly relevant for PEN-200 students.

Obsidian, Taming a Collective Consciousness

tmux is an open-source terminal multiplexer which allows users to manage multiple terminal instances from a single screen. This might not seem groundbreaking if you work from a multi-monitor desktop; however, tmux is a game-changer when you’re managing multiple jobs on a remote Linux system with only shell access. You can split your terminal into multiple panes, reattach to sessions in case a connection drops, or run concurrent background jobs and reconnect to them as needed. Needless to say, it’s an incredibly powerful utility that’s often overlooked. Most PEN-200 students know IppSec from his Hack the Box (HTB) walkthroughs, but his tmux tutorial is just as valuable to OSCP-hopefuls.

https://medium.com/media/29e053edc78f38066dedbcecf7e90de2/href

Lastly, take advantage of every opportunity to sharpen your scripting skills in languages like Python, Bash, PowerShell, and more. Some great use cases would be scheduling tasks on Kali via cron jobs, or automating the process of reconnaissance, post-exploitation enumeration, and credential extraction. As you study, you’ll come across many PoC exploits — some written in languages you don’t know, others that could be improved upon. Instead of settling, why not rewrite the PoC yourself in your preferred language? Not only does this give you a working exploit, but it also becomes a strong addition to your job application portfolio. For inspiration, check out this blog post by a colleague of mine, who developed a working exploit for CVE-2022–35914 after finding the official solution for an OffSec Proving Grounds machine unsatisfactory. When developing scripts or PoCs, consider using a code editor like Visual Studio Code, a popular Microsoft option packed with features and supported languages.

Charting a path to RCE thru PHP callbacks

In short, be proactive when writing your notes. While you may never need to learn an entirely new scripting language, coding platform, or operating system on the fly during a billable engagement, it helps to have a solid grasp of the most useful technologies before landing your first consulting job.

Understand the Real-World Impact of Each Technique

The PEN-200 course provides a thorough and comprehensive foundation in penetration testing. However, applying its techniques in real-world engagements exactly as taught — without considering their potential impact — can lead to unintended consequences. Understanding not just how a technique works but also when, where, and whether to use it, distinguishes a skilled penetration tester from “script kiddies”. This section explores the risks of blindly following course material and how students can develop the judgment necessary to apply techniques responsibly in real-world engagements.

NOTE:

Developing a mature understanding of our tradecraft also helps mitigate the risk of introducing a backdoor through our toolkit. This is demonstrated in a recent CloudSEK report, which revealed that a trojanized version of a remote access Trojan (RAT) malware builder infected 18,459 devices, mostly belonging to cybersecurity students and hobbyists.

OSCP-certified professionals generally agree that PEN-200 does not emphasize stealth. While the syllabus includes an antivirus (AV) evasion module, the course primarily teaches identifying and exploiting vulnerabilities rather than evading detection — likely to prevent overwhelming new students. However, many of these techniques would immediately trigger alerts in security-mature environments. For example, Mimikatz, a popular tool for extracting plaintext credentials and password hashes from Windows Local Security Authority Subsystem Service (LSASS) memory, would almost certainly trigger endpoint detection and response (EDR) alerts if triggered in its original binary form. Many penetration testing techniques face similar scrutiny, and students should understand their OPSEC implications before applying them in real-world assessments.

When people think of service disruption in cybersecurity, their minds often jump to denial of service (DoS) attacks. However, even legitimate penetration testing techniques , if used carelessly, can cause outages and service unavailability. This risk is a major deterrent for businesses considering cybersecurity consulting services, as potential disruptions — such as bandwidth spikes, application latency, or unscheduled downtime — can lead to performance degradation and reputational damage. Common offenders include port scanners like Nmap, vulnerability scanners like Nessus, and brute-force password tools like Kerbrute, which can trigger account lockouts due to repeated failed login attempts. In real-world scenarios, penetration testers must pace network scans carefully, communicate clearly with the client about targeted systems and services, and adhere to account lockout policies to minimize disruptions.

Some tools and techniques can inadvertently expose plaintext credentials or hashed passwords, introducing serious security risks. In a simulated exercise, for example, we might use Mimikatz to dump NT LAN Manager (NTLM) hashes from memory or input a username and password into the Get-Credential PowerShell cmdlet before passing them to a PowerView function. While this may seem harmless in a controlled lab environment, the real-world consequences are far graver. If a Windows host logs command line output or an EDR solution records process activity, these credentials could be stored in logs accessible to administrators, regular users, or even threat actors — potentially leading to credential theft and further malicious actions long after the engagement is complete. Using third-party cloud-hosted tools to process artifacts containing client secrets — such as CrackStation for password hashes or DynamiteLab for packet captures — could also result in credential exposure, as neither the consultants nor the client have control over where that sensitive data is stored.

Lastly, we must consider whether a method could violate personal ethical boundaries or contractual obligations. Cybersecurity consulting firms often establish internal guidelines prohibiting high-risk activities that could cause irreversible damage with little value in a report, such as intentional DoS attacks, disabling security services, unauthorized password changes, or exfiltrating sensitive data like the ntds.dit database or structures containing personally identifiable information (PII). Consultants are also contractually bound by the client-imposed rules of engagement (ROE), which may restrict certain tactics or system/user targets, requiring testers to adjust their tradecraft. For example, Responder, a tool used for capturing NTLM v2 hashes, could unintentionally collect credentials from out-of-scope users or systems, constituting an indirect ROE violation. Ultimately, both personal ethics and professional constraints can significantly impact how penetration testers apply offensive techniques in real-world engagements.

In this section, I’ve explored four critical questions students should ask themselves after becoming proficient with a new security tool or technique:

1. Does this tool/technique carry a high risk of triggering OPSEC solutions?
2. Could this tool/technique result in service disruptions?
3. Could this tool/technique expose plaintext credentials or weak password hashes?
4. How could this tool/technique violate ethical or contractual boundaries?

NOTE:

Other important questions to consider — but omitted for brevity — include: “Would bypassing a common OPSEC solution for this tool/technique require disabling security services?”, “Does this tool/technique leave behind system artifacts that require cleanup to maintain stealth or as part of post-engagement procedures?”, and “Which threat actors have used this tool/technique before?”.

While these questions are important, they should not interfere with your learning process while navigating the course for the first time. Instead, keep them in the back of your mind and revisit them once you have the confidence and time to explore them fully. Developing this awareness early will help ensure you approach offensive security with the professionalism and responsibility expected in real-world engagements.

Read the Footnotes and Follow the Authors

Earlier this year, while preparing for the Offensive Security Experienced Penetration Tester (OSEP) certification, I was working through the PEN-300 course material, a direct continuation of the techniques taught in PEN-200. As I reviewed the footnotes in one of the modules, a particular blog post caught my attention. The topic was interesting, but what really stood out was the author’s handle — it looked vaguely familiar. Curious, I clicked on their profile to dig deeper.

A few seconds later, it hit me. I had accidentally stumbled on my boss’s old blog channel!

This story underscores an important lesson: the footnotes in PEN-200 (and other OffSec courses) aren’t just extra reading material — they’re a window into the offensive security industry. The white papers, PoCs, and blog posts referenced in these courses were written by researchers and hackers who have shaped modern penetration testing techniques and, in some cases, you may even cross paths with them later in your career. Taking the time to explore these citations offers more than just educational enrichment. It provides insight into “who’s who” in the industry, giving you an edge when networking or job hunting. While the extra reading may seem tedious, its benefits are an underappreciated strength of the course.

Understanding who the key players are in offensive security isn’t just an academic exercise; it’s a form of situational awareness that can benefit your career. The individuals whose blog posts and exploit code appear throughout the PEN-200 course are often the same ones presenting at security conferences, contributing to your favorite security tools, or even leading your next interview. The offensive security industry is surprisingly small, so by familiarizing yourself with just a handful of regular contributors, you gain a solid understanding of current industry trends, the companies driving innovation in different areas of cybersecurity, and even what technical skills hiring managers are prioritizing. This awareness can help you make more informed decisions, from identifying career mentors to choosing which companies to apply to.

Once you’ve read the footnote and understood its material, make an effort to follow the author on any platform where they have a public profile. Many security researchers publish their articles on Medium, but it’s also common to find their work cross-posted on personal websites. If the author works at a cybersecurity consulting firm, check their company’s blog — firms like TrustedSec, Mandiant, PortSwigger, and SpecterOps regularly publish security research. If the footnote references a coding project, explore the author’s GitHub profile to see their other work or contributions to open-source projects. Following them on X (formerly Twitter), BlueSky, or LinkedIn ensures you’ll receive timely updates on future publications. Lastly, try searching for the author on YouTube by their full name or handle, as they may have presented at major cybersecurity conferences like DEF CON, Black Hat, or RSA Conference.

Taking the time to read the footnotes and dive into the work of influential security researchers not only enhances the educational value you gain from the PEN-200 course, but also sharpens your situational awareness of the offensive security industry. This knowledge can serve as a powerful networking tool, help you discover new areas of professional interest, and guide your career path. So, next time you come across a footnote, don’t just skim it — take the extra step and use it as a launchpad for further exploration. You might just end up connecting with your next manager…

Conclusion

As always, feel free to comment if you enjoyed the article, have questions/criticisms, or would have liked to see other arguments included. In the next post, I will discuss my advice for the PEN-200 labs.

Getting the Most Value Out of the OSCP: The PEN-200 Course was originally published in Posts By SpecterOps Team Members on Medium, where people are continuing the conversation by highlighting and responding to this story.

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DPRK IT Fraud Network Uses GitHub to Target Global Companies

Nisos is tracking a network of likely North Korean (DPRK)-affiliated IT workers posing as Vietnamese, Japanese, and Singaporean nationals with the goal of obtaining employment in remote engineering...

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Key Takeaways from the CSA Understanding Data Security Risk Survey
madhav
Tue, 03/04/2025 - 04:32

As hybrid and multi-cloud environments become increasingly popular, identifying, prioritizing, and mitigating data security risks becomes increasingly complex. How can we tackle this complexity? By gaining insight into how organizations handle risk. That’s the goal of the latest Cloud Security Alliance (CSA) Understanding Data Security Risk survey, which Thales is a proud sponsor of.

The survey report shares critical insights into the challenges organizations face when managing data security risk and offers actionable steps they can take to secure their most sensitive assets. So, let’s examine some of the key takeaways.

Limited Risk Understanding, Limited Risk Management

Perhaps the most notable revelation from the CSA report is that organizations have gaps in their ability to identify and prioritize vulnerabilities, creating significant challenges in managing data risks.

Statistics from the report drive home the scale of the issue: 31% of respondents say they lack tools to identify their riskiest data sources, while 12% don’t even know if they have such tools. This lack of adequate tooling, among other factors, resulted in 80% of respondents saying they don’t feel highly confident in their ability to identify high-risk data sources.

Other contributing factors include the complexity of hybrid and multi-cloud environments. Over half of the respondents reported operating in hybrid environments, while 27% use multi-cloud setups. The fragmented risk profiles and data distribution inherent in these cloud platforms make it harder to locate and prioritize vulnerabilities and can result in inconsistent management practices.

Organizations can remediate these issues by implementing Thales Data Risk Intelligence capabilities. It unites Thales CipherTrust and Imperva Data Security Fabric platforms to provide a risk score and actionable recommendations for proactively identifying and mitigating risks.

Misaligned Teams, Elevated Risk, Compromised Compliance

The report also reveals that management's strategic priorities aren’t compatible with staff's operational realities. For example, 10% of staff reported being “not at all confident” in identifying high-risk data sources, compared to 3% of management.

Moreover, many executives (41%), perhaps unsurprisingly, want to align security efforts with broader business objectives, all while operational teams are struggling to keep their heads above water, facing resource constraints and relying heavily on manual (22%) or semi-automated (54%) processes.

Clearly, organizations would do well to automate more processes and free up time for operational teams to align their efforts with broader business objectives.

New Risks, New Data-Centric Focus

Despite the wide range of compliance, risk, and security management tools on the market, organizations are struggling to meet the demands of modern data risk management. The problem is that many of these tools aren’t keeping pace with evolving risk management requirements, forcing many (54%) organizations to use four or more tools to manage data risks.

This patchwork approach to risk management results in inefficiencies and conflicting information that can hinder effective decision-making. Thales, however, offers an integrated, holistic approach to risk management and data security. We help organizations move past siloed data protection solutions, providing a centralized and uniform deployment that prepares your organization for the security challenges to come.

Compliance is Important, But Not Sufficient for Proactive Data Security

Regulations and compliance requirements, while the driving force behind most organizations’ (59%) risk reduction strategies are leaving organizations unable to address emerging and evolving risks.

Only 11% of respondents said they prioritize identifying risk behavior, while just 12% focus on adapting to the changing attack surface. Most organizations take a reactive approach to data security that will not be sufficient to protect them from evolving threats.

Therefore, organizations need to partner with security vendors who provide AI-driven innovations and risk-based automations that can help organizations transition to proactive cybersecurity. With Data Risk Intelligence, IT and security teams can quickly discover, classify, and prioritize data based on sensitivity, vulnerability, and risk profiles while proactively protecting at-risk data using encryption and access controls.

A Risk-Based Approach is the Way Forward

More encouraging, however, is organizations’ burgeoning recognition of the limitations of compliance-driven strategies and their steady shift to risk-based approaches: respondents ranked identifying vulnerabilities and prioritizing vulnerabilities as their two highest policies, far outpacing activities such as changing policies and controls. Similarly, respondents reported valuing key performance indicators like vulnerability patch rate (36%) and security violations (35%) over compliance violations (29%), further highlighting their commitment to risk-based strategies rather than compliance-driven ones.

Thales has all the solutions you need to switch to a proactive, risk-focused approach to data security. Our advanced data activity monitoring, data risk analytics, risk posture management, data encryption, key management, network encryption, hardware security module, and data protection on-demand solutions enable customers to protect and remain in control of their data wherever it resides – across cloud, on-premises, and hybrid IT environments.

Get your copy here of the CSA Understanding Data Security Risk report.
Want to find out more about what we can do for your organization? Contact us today.

Together, these actions provide a clear roadmap for navigating today’s complex risk landscape and protecting critical data assets.

Data Security Compliance Regulation and compliance Encryption

Lynne Murray | Director of Product Marketing for Data Security
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basic

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San Francisco, Calif., Mar. 3, 2025, CyberNewswire — With the growing importance of security compliance for startups, more companies are seeking to achieve and maintain compliance with frameworks like SOC 2, ISO 27001 & GDPR.

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Author/Presenter: Rachel Cummings

Our sincere appreciation to DEF CON, and the Authors/Presenters for publishing their erudite DEF CON 32 content. Originating from the conference’s events located at the Las Vegas Convention Center; and via the organizations YouTube channel.

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via the comic humor & dry wit of Randall Munroe, creator of XKCD

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