Getting the Most Value Out of the OSCP: The Exam

A practical guide to maximizing the short- and long-term benefits of your upcoming OSCP exam attempt(s).

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 the last post in this series, I discussed a few proactive steps students should take throughout the PEN-200 labs as part of their efforts to earn the Offensive Security Certified Professional (OSCP) certification. In this entry, let’s focus on test day itself — and how to maximize the educational, financial, and professional value of the OSCP exam experience.

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

During the Exam(s)…

“You may be disappointed if you fail, but you are doomed if you don’t try.” — Beverly Sills

Congratulations — you’re now ready to take the OSCP exam! Despite being the shortest of the five phases in the “OSCP journey”, there are still important steps you can take to ensure you’re getting your money’s worth. Here are three key takeaways for all future exam-takers:

1. The OSCP exam is designed to mimic a black-box penetration test, but due to the nature of standardized testing, it inevitably falls short of being a perfect replica of a real-world engagement; while this is completely reasonable, it helps to be prepared to speak to these nuances in future job interviews and not to confuse exam-specific tactics with best practices in the field
2. Certification exams — for better or worse — play a role in many offensive security consulting careers, so it’s best to set a precedent for sustainable and practical test-taking behavior by developing realistic, ethical, and repeatable exam-day practices and using them during your OSCP attempt(s)
3. Follow OffSec’s exam-day instructions to the letter, as even minor deviations could invalidate months (or years) of work toward the OSCP and may disqualify you from future OffSec certifications

Understand the Differences Between the OSCP Exam and Real-World Practice

While the OSCP exam certainly tests your offensive security knowledge, it’s important to understand what the exam is and isn’t. OffSec has gone to great lengths to make the OSCP a realistic simulation of a black-box penetration test; however, to ensure fair grading and timely results, it comes with inherent limitations. By recognizing these gaps ahead of time, students can better interpret their exam experience, set realistic expectations for future consulting roles, better articulate their skills in interviews, and avoid drawing the wrong conclusions about what the certification does (or doesn’t) prove to a technical recruiter.

While not an exhaustive list, here are the differences I consider the most significant to keep in mind:

• Team Collaboration: Although the OSCP exam is a solo endeavor, operators seldom work alone in real-world engagements; exceptions may exist for engagements with extremely limited scope or niche objectives, but most involve at least two consultants

• Client Interaction: During the exam, your only contact is with the OSCP proctor(s); in a real engagement, you should expect to interact with business managers, engineers, security operations center (SOC) employees, and a designated point of contact (POC) throughout the lifecycle of a client-consultant relationship
• Scope Definition and Rules of Engagement (ROE): While the Exam Restrictions in the exam guide could be interpreted as a partial ROE, real-world assessments include far more comprehensive documentation and legal implications for its violations; consultants may also be involved in negotiating the scope of upcoming engagements
• Engagement Objectives and Metrics: The objective of the OSCP exam is to gain initial and elevated access to as many systems as possible; in contrast, real-world assessments may involve more targeted objectives, like exfiltrating dummy data, compromising specific users or systems, bypassing defenses, or demonstrating how vulnerabilities are tied to business impact
• Operating with Due Caution: Whereas the OSCP exam gives candidates near-total freedom within the simulated network (aside from a few restricted attacks and tools), real-world consultants must consider the impact of their actions on live systems and people, adapting their approach as needed; consultants will often request POC approval before executing commands that could trigger account lockouts or system downtime
• Deconfliction: If an attack is detected, SOC teams may raise a deconfliction event to confirm it was part of the assessment; if not confirmed, the alert could trigger a full-scale incident response process

• Post-Engagement Procedures: After the OSCP exam, the student’s only obligation is to submit a report; in contrast, wrapping up legitimate consulting engagements may involve artifact cleanup, resolving deconfliction events, stakeholder presentations, blue team debriefs, infrastructure teardown, and secure data destruction
• Cloud-Hosted Tools: Using third-party or cloud-hosted tools to process clients’ artifacts — such as for reverse engineering, data exfiltration, or hash cracking — carries the risk of exposing secrets to systems beyond client or consultant control; because the OSCP exam uses entirely fictional data, its restrictions around cloud usage are more flexible
• Timeline: The OSCP exam splits the practical and reporting components into two ~24-hour phases that test a candidate’s ability to rapidly identify, exploit, and document vulnerabilities; in contrast, real-world engagements typically span several weeks per phase depending on scope and client expectations

• Threat Modeling: Some assessments require consultants to emulate specific threat actors by using a tailored subset of tactics, techniques, and procedures (TTPs); during the OSCP, students are not bound by these constraints
• Kali Linux Requirement: The OSCP must be completed using a Kali Linux VM, but while Kali is a popular Linux distribution for ethical hacking, its large toolset increases both operational overhead and the probability of detection; real-world operators often use custom minimal Linux builds with obfuscated toolkits deployed via continuous integration and continuous delivery/deployment (CI/CD) pipelines to reduce both detection risk and scaling costs
• Social Engineering: While the OSCP exam may involve limited client-side attacks (an assumption based on the fact that there is a “Client-Side Attacks” module in the publicly available syllabus), its highly automated structure means it offers few opportunities to exploit the weakest link in any cybersecurity program: the human element; in real-world assessments, consultants may use tactics like spear-phishing, vishing, or smishing (if the ROE permits it) to achieve credential access or arbitrary code execution (ACE) capabilities
• Physical Security: Some assessments allow physical intrusion tactics — such as piggybacking/tailgating or lock-picking — to gain access to critical infrastructure and test physical security controls; while not feasible during the OSCP exam and somewhat niche, it’s still valuable to conceptually understand these attack vectors

The OSCP is an achievement to be proud of, but it doesn’t perfectly mirror professional practice. Keeping these differences in mind, students can more accurately frame their OSCP experience, communicate their skills more effectively, and set realistic expectations for job responsibilities. Recognizing its limitations is a critical step toward bridging the gap between certification and your career.

Develop Healthy Exam Habits

If this is your first multi-day practical exam, it’s best to build healthy habits and eliminate disruptive ones early. This sets you up for long-term success and a better experience in future exams, regardless of which certification you’re pursuing.

The OSCP exam, for those unfamiliar, is a grueling ordeal. It begins with a 23-hour, 45-minute technical assessment where the student must exfiltrate a minimum number of flags from six machines. Three of these are standalone targets that require the student to complete the full attack path — from initial access to privilege escalation. The other three form an Active Directory (AD) set, where the student is ceded access as a lower-privileged user and escalates to Domain Admin or equivalent-level access. To pass, students must capture enough flags to reach at least 70 out of 100 points (each flag is worth 10 points). They’re then given ~24 more hours to submit a professional report detailing how they achieved each objective. Needless to say, it’s an exhausting endeavor and a major source of stress for many.

As painful as it is to admit, the OSCP — for all its notoriety and difficulty — is considered an entry-level certification in offensive security consulting. It covers a wide breadth of knowledge but ultimately scratches the surface of or doesn’t attempt to address topics like evading operational security (OPSEC) solutions, deploying and maintaining command and control (C2) infrastructure, and identifying more advanced vulnerabilities, to name a few. While certifications aren’t strict gatekeepers to the industry or career advancement, an employer may eventually require you to pursue more advanced practical exams (or you may feel pressured to do so to stay competitive in the job market). With that in mind, and especially if the OSCP is your first multi-day practical exam, it’s in your best interest to develop sustainable exam habits early on to avoid building a detrimental relationship with certifications.

Let’s start with the simplest, yet arguably hardest, topic: sleep. While it may be tempting to pull an all-nighter and grind through flags as quickly as possible, this approach is likely counterproductive. Research consistently show that sleep deprivation impairs cognitive functioning, stifles creativity, and slows reaction times — all of which are essential during the OSCP exam. Some studies even suggest that sleeping more than usual the night before a test is correlated with better performance. For multi-day exams, I aim for at least eight hours of sleep each night, regardless of how much progress I made the day before. If you’re interested in the science behind sleep, I highly recommend Why We Sleep by Matthew Walker, PhD.

Your exam success largely depends on the quality of your notes. Make a habit of taking structured, detailed, and legible notes throughout your technical challenges. Consider building a note template in a node-based application like Obsidian and refining it during a few PEN-200 labs or Hack the Box (HTB) machine exercises. The more structure you establish in advance, the more mental bandwidth you preserve on exam day. Effective note-taking is a transferable skill that strengthens both your technical execution and report-writing abilities as an offensive security consultant.

A few days before an exam, I like to deep clean my office — starting with vacuuming the floors and finishing by decluttering my workspace. A minimalist setup not only supports compliance with OffSec’s exam policies (more on that later), but also fosters a calmer mental space where you can think clearly and move efficiently. I also recommend silencing your phone, placing it out of reach, notifying others that you’ll be unavailable, and using noise-canceling headphones if you’re in a shared household. The fewer distractions in your space, the easier it is to focus on solving complex problems.

The tight 24-hour window of the OSCP exam demands a strategic approach to time management. Techniques like the Pomodoro Technique — working in focused sprints followed by short breaks — can help prevent burnout and minimize the risk of losing hours chasing rabbit holes. Even if you choose not to use a formal time-management method, entering the exam with a clear plan is far more effective than charging in with a purely reactive mindset. Some approaches that merit attention include capping your focus on a single challenge to 60–90 minutes before pivoting to another, or pre-allocating specific blocks of time to each machine/challenge set in the exam.

Your time-management strategy should also account for the maintenance of your own body: plan your meals in advance, step away from the screen while eating, and stay well hydrated. If possible, build in time on test-day for light aerobic activity — such as a quick jog, a walk with the dog, or a short set of bodyweight exercises like jumping jacks, mountain climbers, or burpees. Brief physical movements can help re-energize your mind, reduce stress, and boost cognitive performance.

To help anchor your experience and reduce anxiety, consider designing personal pre- and post-exam rituals. The night before, do something relaxing — like casually reviewing your notes, solving an easy HTB machine, or writing encouraging Post-it notes to stick on your wall. Set your clothes, snacks, and water up like you’re getting ready for a marathon — because in many ways, you are. After the exam, give yourself a buffer to recover, reflect, and decompress. Personally, I like to go out with friends, play nostalgic video games, or grab a Guinness. Whatever your rituals look like, make them personal and genuinely rewarding.

Finally, I encourage all students to embrace the result of the exam, pass or fail. The OSCP is not the final word on your skills — it’s a checkpoint, not a verdict. In fact, failing by a narrow margin can often be more educational — and ultimately more empowering — than barely passing. By adopting a growth mindset, you can view a missed attempt not as a reflection of your limitations, but as an opportunity to walk away with clearer insight into your strengths and gaps. This self-awareness can be carried with confidence into job interviews, real-world engagements, and the refinement of your study plan. We’ll explore this topic more deeply in the next post.

Building sustainable and empowering exam habits isn’t just about getting through a difficult 24 hours; it’s about establishing a process you can carry into future certifications, real-world assessments, and high-stakes professional challenges. By developing tenable and fulfilling exam-day practices with intent, you give yourself the best possible chance to succeed — not just in the exam, but in the career that follows.

Don’t Risk Your Exam Attempt

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The OSCP certification is a multi-thousand dollar investment, so the last thing any student wants is to have their attempt invalidated due to a preventable mistake or misunderstanding that results in an accusation of academic misconduct. Rather than viewing the exam solely as a test of technical skill, candidates should approach it as a professional engagement with clearly defined operational and ethical boundaries. To safeguard the time, effort, and money you’ve invested in the OSCP journey, it’s imperative to read every instruction carefully, double-check your testing environment, and follow OffSec’s exam-day guidelines to the letter.

As one of the most recognized credentials in cybersecurity, the OSCP carries significant industry weight — and OffSec therefore takes the integrity of its exam process seriously. In 2018, in response to growing concerns about cheating, OffSec introduced an online proctoring system to the exam. Candidates are required to verify their identity with a government-issued ID and maintain continuous screen sharing and webcam visibility during the first ~24 hours of the exam.

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In 2019, an individual using the handle cyb3rsick publicly released write-ups for several retired OSCP exam machines, reportedly in protest of the exam’s format, which they claimed “allowed thousands of [students] to cheat and pass the exam”. Coverage of the incident highlighted both the controversy and the industry’s reaction. In response, OffSec published a blog post that provided insight into the organization’s anti-cheating measures. These include: relying on community reports, monitoring suspicious groups or individuals, modifying exam systems on a “regular basis”, using undisclosed detection mechanisms during grading, and online proctoring. Most notably, OffSec emphasized that cheaters may face severe consequences — including potential legal action. As stated in their post, “cheaters have lost their certs, paid fines, lost their jobs, and been embarrassed in front of their peers”.

Some stories involving failed exam attempts, revoked certifications, or bans appear to stem from accidental missteps rather than deliberate misconduct. While it’s clear that OffSec has taken meaningful action against individuals who have knowingly violated academic integrity policies, it’s also reasonable to acknowledge that some cases may result from honest mistakes, misunderstandings, or technical issues. One example occurred in 2019, when a student used the common Linux/Unix* post-exploitation enumeration tool, LinPEAS, during their exam. At the time, a recent update to the script had introduced an auto-exploitation feature, which resulted in the student escalating privileges immediately on the target host. Because the Exam Restrictions prohibit the use of tools with auto-exploitation capabilities, the student initially received a failing grade. OffSec later addressed the incident in a blog post, and the student reportedly had their result overturned and was awarded a passing grade. There have also been multiple incidents of students losing their certifications after their private exam reports were leaked or stolen and subsequently used by others to cheat — an issue OffSec has acknowledged in their Support Portal.

This section is not intended to criticize or undermine OffSec’s authority to vigorously pursue cases of academic misconduct or copyright infringement, but rather to inform aspiring OSCP-certified professionals — especially those acting in good faith — on how to conduct themselves confidently and transparently on exam day.

To align with OffSec’s expectations for a successful exam day, I recommend the following:

• Revisit the OSCP Exam Guide and PEN-200 Reporting Requirements a week or two before your exam; consider incorporating them into a Requirements or Rules of Engagement section in your report template to reinforce them into memory
• Keep the proctoring window visible at all times, reply promptly to requests, and reconnect your camera immediately if it becomes disconnected
• Remove unnecessary items from your workspace, such as additional screens (OffSec permits up to four monitors during the exam), notebooks, smart devices, or inactive laptops
• Store your phone in a separate room and notify others that you’ll be unreachable during the exam

• Before the exam, take inventory of your toolkit and review each utility’s documented functionality to ensure it doesn’t include features that OffSec prohibits (e.g., spoofing, automatic exploitation, commercial services) and keep a record of any new tools you use during the exam; this level of caution is also applicable to real-world engagements, where it is important to fully understand the behavior and implications of the tools you deploy in a client environment
• Keep all notes local; avoid accessing documents stored on cloud platforms (e.g., GitHub, GitLab, or OneNote)
• Terminate unnecessary screen-sharing programs (e.g., Discord, Zoom, Teams); even idle background processes can raise red flags
• Use a single device and identity throughout the exam; ensure the name on your ID matches your OffSec registration details, complete the exam on a single authorized system, and terminate any third-party virtual private network (VPN) applications — as changing IP addresses mid-exam may be interpreted as location switching

• Minimize physical and digital movement; don’t leave the camera’s view without telling the proctor, and avoid switching desktops, using unrelated virtual machines (VMs), or removing hardware devices
• Never download artifacts from the exam environment to your local machine; all work should remain within your VM
• Be mindful of physical cues that might appear suspicious on camera, such as repeated glances away from the screen, whispering, interacting with unmonitored people, or unexplained movements

• If you’re referencing notes from a previous attempt, inform the proctor to distinguish it from reused or plagiarized content
• Have a backup device and mobile hotspot ready in case of system failure or internet loss
• Consider creating a clean system user profile just for the exam to reduce redundant applications and protect your privacy

If, despite following this advice, you’re still found guilty of academic misconduct, stay calm and professional. Cooperate fully with the investigation, be honest and transparent, and avoid becoming defensive — it’s important not to escalate the situation. Instead, politely request specific details regarding the accusation, seek to understand the exact concerns, and explain any misunderstood behavior or tools (e.g., a tool that was not on the shortlist of restricted software but raised concern). If you’re unsatisfied with the outcome, wait a week or two to cool off before submitting a formal appeal to challenges [at] offsec [dot] com. Maintain the same professional and respectful tone in your appeal as you did during the investigation.

On a final note, it’s important to acknowledge that OffSec exams involve a high degree of monitoring. Your screen is shared throughout the exam, you’re under near-continuous video surveillance, and you must perform a 360-degree scan of your workspace to confirm that no unauthorized devices or individuals are present. Before beginning the exam, Windows users are required to execute a proctor-provided PowerShell script that gathers system information and lists running processes — likely to flag potentially unauthorized tools. Out of an abundance of caution, it’s a good idea to clean up your local system before exam day; remove any personal files or unfamiliar tools that could trigger concern. For more details on how OffSec collects and processes personal data, refer to their Privacy Policy.

OffSec has every right (and responsibility) to uphold the integrity of its certification, but that doesn’t make the proctoring process any less stressful for honest students. Trying to be diplomatic while raising a nuanced point, it’s fair to say that even well-intentioned candidates may find themselves under scrutiny. By taking proactive steps to minimize ambiguity in your environment and interactions with the proctors, you not only protect your OSCP investment but also reinforce the professional habits OffSec aims to instill through its arduous exam process.

NOTE:

If you’re uncomfortable with the format or privacy implications of the OSCP exam, you might consider alternatives like the Certified Red Team Operator (CRTO) or Practical Network Penetration Tester (PNPT). These certifications cover similar material and offer more flexible testing policies.

Conclusion

Feel free to leave a comment with any questions, feedback, or additional advice to contribute to this discussion. In the final post of this series, I’ll cover what students should do after each OSCP exam attempt — whether they pass or not.

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

The post Getting the Most Value Out of the OSCP: The Exam appeared first on Security Boulevard.

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