Introduction

OffSec is marking two decades as a provider of practical cybersecurity education. Founded in 2006 by security professionals who believed in learning by doing, the company has become known for Kali Linux, the OSCP certification, and a Try Harder mindset that emphasizes persistence under pressure. CEO Ning Wang says the core mission remains unchanged: develop critical thinkers and problem solvers who can perform when systems are under attack.

What Happened

The anniversary announcement traces OffSec's roots to 2006, when cybercrime was emerging as a major industry. The organization grew out of the security community itself, with founders who wanted to teach through direct experience rather than theory alone.

Over the years, OffSec has built several widely used resources. BackTrack Linux evolved into Kali Linux in 2013, offering a free platform for penetration testing, research, forensics, and reverse engineering. Kali Purple followed in 2023 to support defensive security work. The OSCP certification became a benchmark for penetration testing because candidates must compromise live systems and document their findings. OSCP+, a renewable version of the credential, arrived in 2024.

Other milestones include the 2009 launch of the Exploit Database, a free public archive of exploits and security research, and the acquisition of VulnHub. OffSec also offers free labs through Proving Grounds Play and recently introduced HackTrack, a 10-week live training program. The first HackTrack cohort focused on OSCP, while an upcoming edition will cover OSAI.

To mark the anniversary, OffSec is offering individual practitioners a limited-time 20 percent discount on Learn One annual subscriptions.

Why This Matters

The cybersecurity landscape looks very different than it did in 2006. Attackers now use artificial intelligence to find and weaponize vulnerabilities faster than ever, and the window between a vendor patch and a working exploit continues to close. At the same time, many organizations struggle to find skilled staff.

ISC2's 2025 Cybersecurity Workforce Study found that 95 percent of organizations report at least one skills gap, with 59 percent describing those gaps as critical or significant. That figure rose from 44 percent in 2024. OffSec argues that annual compliance training is no longer enough and that teams need continuous, hands-on development.

CEO Ning Wang highlighted this point during an October 2026 keynote at Singapore International Cyber Week, telling attendees that working through difficult problems early builds the confidence and resilience needed for long-term success.

Key Takeaways

  • OffSec was founded in 2006 and is celebrating 20 years of practitioner-led cybersecurity training.
  • The organization created Kali Linux and the OSCP certification, both widely recognized in the security industry.
  • OffSec maintains free resources such as the Exploit Database and Proving Grounds Play, and recently added HackTrack live training.
  • ISC2 data shows a growing skills gap, with 59 percent of organizations calling their gaps critical or significant in 2025.
  • OffSec is prioritizing AI-era learning and plans to release updated courses for the coming year.

Conclusion

Two decades after its founding, OffSec is positioning itself for the next phase of cybersecurity education. The company has expanded from offensive security into a broader workforce development portfolio, including Learn Enterprise with 14 certifications, more than 125 learning paths, and 8,000 hours of content mapped to frameworks such as NICE and DCWF. In 2026, it also launched Live Training, sending instructors on site to work with security teams in realistic scenarios.

Looking ahead, OffSec says AI literacy will be central to its curriculum. As Wang put it, defending against AI-driven threats requires security teams that understand how to use AI themselves. Organizations interested in enterprise training can request a demo through OffSec's website.