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OSAI

OffSec AI Red Teamer (AI-300)

Offensive Advanced OffSec
Target job title
AI Red Teamer / AI Security Engineer
Level
Advanced. Built for practitioners with real experience; often hard experience gates.
Prerequisites
OSCP-level offensive skills, Python, and working knowledge of LLM applications, RAG and AI agents.
Official page
OffSec

Recent updates

AI-300 launched in 2026. Passing the proctored practical exam against an AI-enabled enterprise environment awards OSAI plus the 3-year OSAI+.

Reviewed 2026-10-02. Source. Confirm exam details on the official page before booking.

Where it sits in Offensive Security

  1. Entry CRTA CEH OSWP eJPT TryHackMe PT1 HackTheBox CJCA
  2. Intermediate OSCP HackTheBox CPTS CRTP OSWA CompTIA PenTest+ eCPPT TCM PNPT HackTheBox CWES CRTO BSCP GPEN CARTP
  3. Advanced CRTE OSEP OSED OSAI HackTheBox CAPE TryHackMe PT2 OSWE
  4. Expert HackTheBox COAE CRTL OSEE HackTheBox CWEE

Natural next steps: HackTheBox COAE, CRTL, OSEE, HackTheBox CWEE.

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