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Certifications & Emerging Trends

16 min read

Certifications & Emerging Trends

The red teaming discipline is evolving rapidly. Practitioners must invest in continuous skill development through structured certifications while staying ahead of emerging trends that reshape how engagements are scoped, executed, and defended against. This page covers the certification landscape, recommended training paths, and the forces transforming offensive security — from AI-assisted operations to zero trust architectures.

For foundational red team concepts, see Fundamentals. For tool-specific guidance that complements certification training, see Tools Reference.


Certification Landscape Overview

Why Certifications Matter for Red Teamers

Certifications serve multiple purposes in the offensive security community. They are not just resume items — the best offensive certifications are practical proof of capability. Unlike many IT certifications built around multiple-choice exams, the most respected red team certifications require candidates to demonstrate hands-on exploitation skills under time pressure.

Practical vs. Theoretical Value

The offensive security community strongly favors practical, exam-based certifications over purely theoretical ones. A certification that requires breaking into machines within a time limit carries far more weight than one based solely on memorizing concepts. Employers and peers recognize this distinction. When evaluating certifications, prioritize those with hands-on lab components and practical exams.

Employer Expectations

Depending on the employer and role level, expectations vary:

  • Entry-level red team roles: OSCP is widely considered the baseline. Some employers accept PNPT or equivalent practical certifications.
  • Mid-level positions: OSCP plus a specialization cert (CRTO, CRTP, OSEP) demonstrates depth.
  • Senior roles: A combination of certifications, published research, conference talks, and demonstrated engagement experience matters more than any single cert.
  • Government and defense contracting: GPEN and other GIAC certifications are often contractually required, sometimes regardless of skill level.

Building a Certification Path

Approach certifications strategically. Avoid collecting certs randomly — instead, build a coherent path that reflects the areas you want to specialize in. Assess your current skill level honestly, identify gaps, and select certifications that address those gaps while opening doors to the roles you want.


Certification Deep Dives

OSCP — OffSec Certified Professional

Provider: Offensive Security (OffSec) Course: PEN-200 (Penetration Testing with Kali Linux)

The OSCP remains the most widely recognized offensive security certification. It is the de facto standard that most employers use as a baseline filter for penetration testing and red team candidates.

Prerequisites: Solid understanding of networking (TCP/IP, routing, firewalls), comfort with Linux command line, basic scripting ability (Python, Bash), and familiarity with common vulnerabilities. OffSec recommends their PEN-100 or equivalent experience.

Exam Format: A 23-hour and 45-minute practical exam where candidates must compromise a series of standalone machines and an Active Directory set. Points are earned for each machine compromised, with bonus points available for submitting a professional-quality report. The passing score is 70 points. Candidates must demonstrate the exploitation without relying on automated tools like Metasploit (limited to one use).

Coverage: Enumeration, web application attacks, buffer overflows (Windows and Linux), privilege escalation, Active Directory attacks, client-side attacks, tunneling and pivoting, and basic post-exploitation.

Difficulty: Intermediate. The exam is challenging but achievable with dedicated preparation. Most successful candidates spend 3-6 months preparing, combining the course materials with platforms like HackTheBox, TryHackMe, and Proving Grounds.

Community Perception: Highly respected as a foundational cert. The “Try Harder” ethos associated with OSCP is embedded in the offensive security culture. However, experienced practitioners note that OSCP alone does not make someone red-team-ready — it is a strong starting point.

Preparation Resources:

  • OffSec PEN-200 course materials and lab environment
  • TJnull’s OSCP-like machine list on HackTheBox and Proving Grounds
  • IppSec YouTube walkthroughs for methodology development
  • Proving Grounds Practice (OffSec’s own practice platform)

OSEP — OffSec Experienced Penetration Tester

Provider: Offensive Security (OffSec) Course: PEN-300 (Evasion Techniques and Breaching Defenses)

OSEP builds on OSCP by focusing on the techniques needed when defenses are actively resisting you. This is where you learn to operate against mature security environments.

Advanced Topics:

  • Antivirus and EDR evasion techniques
  • Custom shellcode development and encoding
  • Process injection and process hollowing
  • Advanced Active Directory attacks (delegation abuse, trust relationships)
  • Microsoft SQL Server attacks
  • AMSI bypass techniques
  • Application whitelisting bypass
  • Lateral movement in hardened environments

Exam Format: A 47-hour and 45-minute practical exam. Candidates must compromise a multi-machine Active Directory environment with mature defenses in place. The exam requires chaining multiple techniques to achieve objectives, closely mirroring real-world red team operations.

Who It’s For: Practitioners who have completed OSCP (or equivalent) and want to advance into red team roles where bypassing modern defenses is essential. This cert separates penetration testers from red teamers.

Community Perception: Very well regarded. Passing OSEP demonstrates that a candidate can operate against defended environments, not just vulnerable ones.


CRTO — Certified Red Team Operator

Provider: Zero-Point Security (developed by Daniel “RastaMouse” Sherlock) Course: Red Team Ops

CRTO has rapidly become one of the most recommended certifications for aspiring red teamers, particularly for its practical focus on command-and-control operations and Active Directory attack chains.

Key Focus Areas:

  • Cobalt Strike usage and configuration (malleable C2 profiles, listeners, beacons)
  • Active Directory enumeration and attack chains
  • NTLM relay attacks and Kerberos abuse
  • Lateral movement techniques
  • Host and network privilege escalation
  • Data exfiltration and operational security

Lab Environment: Candidates get access to a Snap Labs environment running a realistic corporate Active Directory network with Cobalt Strike licenses. This hands-on lab time is where most of the learning happens.

Exam Format: A 48-hour practical exam in a dedicated lab environment. Candidates must collect flags by compromising machines and escalating privileges across the environment. The exam uses a Cobalt Strike team server, mirroring real red team operations.

Cost and Accessibility: Significantly more affordable than SANS or OffSec alternatives. The course and exam are priced accessibly, making it an excellent value proposition. Course access is typically offered in fixed periods (e.g., 30 or 60 days of lab time).

Community Perception: Extremely well regarded. Practitioners praise its real-world applicability and the quality of the course content. The Cobalt Strike focus is both a strength (it mirrors professional red team tooling) and a limitation (not everyone uses Cobalt Strike).


CRTP — Certified Red Team Professional

Provider: Altered Security (formerly Pentester Academy) Course: Active Directory Attacks Lab

CRTP is a focused certification built around Active Directory attacks, making it an excellent foundational cert for anyone entering red teaming or internal penetration testing.

Key Focus Areas:

  • Active Directory enumeration (BloodHound, PowerView, ADModule)
  • Privilege escalation in AD environments
  • Kerberoasting, AS-REP roasting
  • Unconstrained, constrained, and resource-based constrained delegation
  • Forest and domain trust attacks
  • Persistence mechanisms (Golden Ticket, Silver Ticket, DSRM, ACL abuse)

Lab Environment: Hands-on lab with a multi-domain Active Directory forest. Candidates work through attack chains using both manual techniques and tooling.

Exam Format: A 24-hour hands-on exam requiring candidates to compromise an AD environment by chaining multiple attack techniques. A report is also required.

Value Proposition: CRTP provides an excellent foundation in AD attacks at a reasonable price point. It is often recommended as a stepping stone before CRTO or OSEP, particularly for candidates who need to strengthen their AD knowledge.


GPEN — GIAC Penetration Tester

Provider: GIAC (Global Information Assurance Certification) Course: SANS SEC560 (Enterprise Penetration Testing)

GPEN is the SANS/GIAC offering for penetration testing and carries significant weight in enterprise and government environments.

Coverage: Network penetration testing, web application attacks, password attacks, reconnaissance, scanning, exploitation, and post-exploitation. Broader in scope than OSCP but with less depth in any single area.

Exam Format: A proctored, multiple-choice exam (82 questions, 3 hours). Candidates can use an open-book index. While the exam is not hands-on, SEC560 includes substantial lab exercises.

Cost: The most expensive option on this list. SANS training plus GIAC exam fees typically run several thousand dollars. Employer sponsorship is common.

Employer Value: Very high in corporate, government, and defense sectors. GPEN satisfies DoD 8570 requirements and is recognized by organizations that mandate GIAC certifications contractually.

Community Perception: Respected for the quality of SANS training, but some practitioners feel the exam format does not adequately test practical skills. The knowledge gained from SEC560 is valuable regardless.


GXPN — GIAC Exploit Researcher and Advanced Penetration Tester

Provider: GIAC Course: SANS SEC760 (Advanced Exploit Development for Penetration Testers)

GXPN represents the advanced end of the GIAC offensive certification path.

Coverage:

  • Custom exploit development (Windows and Linux)
  • Shellcode writing and encoding
  • Return-oriented programming (ROP) and bypass techniques
  • Heap exploitation
  • Advanced fuzzing techniques
  • Network protocol reverse engineering
  • Patch diffing and vulnerability discovery

Exam Format: Proctored exam, 60 questions, 3 hours. Open-book with index.

Who It’s For: Experienced penetration testers and red teamers who want to move into exploit development and vulnerability research. This is not a beginner certification.

Community Perception: Highly respected for the depth of technical knowledge required. The SEC760 course content is considered among the best available for exploit development training.


Other Notable Certifications

CRTL — Certified Red Team Lead (Zero-Point Security) The advanced follow-up to CRTO, covering red team management, multi-team operations, and advanced C2 infrastructure. Designed for those moving into team lead roles.

PNPT — Practical Network Penetration Tester (TCM Security) An affordable, practical certification covering external and internal penetration testing, OSINT, and Active Directory attacks. The exam includes a unique requirement to deliver a professional debrief to a mock client. Excellent for beginners entering the field.

eCPTX — eLearnSecurity Certified Penetration Tester eXtreme (INE) An advanced penetration testing certification with a challenging multi-day practical exam. Covers advanced AD attacks, custom tool development, and evasion. Well-regarded but less commonly seen than OSEP or CRTO.

CARTE — Certified Azure Red Team Expert (Altered Security) Focused specifically on Azure and Entra ID (formerly Azure AD) attacks. Covers Azure service exploitation, managed identity abuse, Azure AD attack chains, and cloud-specific persistence. Increasingly relevant as organizations migrate to cloud.


Certification Comparison Table

CertificationProviderFocus AreaExam TypeDurationApproximate CostDifficultyPrerequisitesRenewal
OSCPOffSecGeneral pentesting, ADPractical (machines)24 hours$1,749+IntermediateNetworking, Linux, scripting3 years (CPE)
OSEPOffSecEvasion, advanced ADPractical (AD chain)48 hours$1,749+AdvancedOSCP or equivalent3 years (CPE)
CRTOZero-Point SecurityC2 operations, ADPractical (flags)48 hours~$500Intermediate-AdvancedBasic AD knowledgeNone (lifetime)
CRTPAltered SecurityActive DirectoryPractical (AD chain)24 hours~$300-500IntermediateBasic pentesting3 years
GPENGIAC/SANSEnterprise pentestingProctored MCQ3 hours$5,000+ (with training)IntermediateGeneral IT experience4 years (CPE)
GXPNGIAC/SANSExploit developmentProctored MCQ3 hours$5,000+ (with training)ExpertGPEN or strong exploit dev4 years (CPE)
PNPTTCM SecurityPractical pentestingPractical + debrief5 days + 2 days~$400Beginner-IntermediateBasic IT knowledgeNone
CRTLZero-Point SecurityRed team leadershipPractical48 hours~$500AdvancedCRTO recommendedNone (lifetime)
eCPTXINEAdvanced pentestingPracticalMulti-day$400+AdvancedeCPTXv1 or equivalentSubscription
CARTEAltered SecurityAzure/Cloud ADPractical24 hours~$300-500Intermediate-AdvancedAzure basics, CRTP helps3 years

Training Paths

The following diagram illustrates recommended certification paths based on career goals and current skill level.

graph TD
    A["<b>Starting Point</b><br/>Assess Current Skills"] --> B{"Experience<br/>Level?"}

    B -->|"Beginner"| C["<b>PNPT</b><br/>TCM Security<br/>Practical foundations"]
    B -->|"Intermediate"| D["<b>OSCP</b><br/>OffSec<br/>Industry standard"]
    B -->|"Experienced"| E["<b>OSEP</b><br/>OffSec<br/>Evasion & advanced AD"]

    C --> D
    D --> F{"Specialization<br/>Goal?"}

    F -->|"Red Team Ops"| G["<b>CRTO</b><br/>C2 & Operations"]
    F -->|"AD Specialist"| H["<b>CRTP</b><br/>AD Foundations"]
    F -->|"Exploit Dev"| I["<b>GXPN</b><br/>Exploit Research"]
    F -->|"Cloud"| J["<b>CARTE</b><br/>Azure Red Team"]

    G --> K["<b>OSEP</b><br/>Evasion Techniques"]
    H --> G
    G --> L["<b>CRTL</b><br/>Red Team Leadership"]
    K --> L
    H --> K
    I --> M["<b>Custom Research</b><br/>CVE discovery, tooling"]
    J --> N["<b>Cloud Vendor Certs</b><br/>AWS/Azure/GCP Security"]

    style A fill:#2d3748,stroke:#4a9eff,color:#fff
    style B fill:#1a202c,stroke:#f6ad55,color:#fff
    style F fill:#1a202c,stroke:#f6ad55,color:#fff
    style C fill:#2d3748,stroke:#68d391,color:#fff
    style D fill:#2d3748,stroke:#68d391,color:#fff
    style E fill:#2d3748,stroke:#68d391,color:#fff
    style G fill:#2d3748,stroke:#63b3ed,color:#fff
    style H fill:#2d3748,stroke:#63b3ed,color:#fff
    style I fill:#2d3748,stroke:#63b3ed,color:#fff
    style J fill:#2d3748,stroke:#63b3ed,color:#fff
    style K fill:#2d3748,stroke:#b794f4,color:#fff
    style L fill:#2d3748,stroke:#fc8181,color:#fff
    style M fill:#2d3748,stroke:#fc8181,color:#fff
    style N fill:#2d3748,stroke:#fc8181,color:#fff

Beginner Path

PNPT → OSCP → CRTP

Start with PNPT to build practical foundations without excessive difficulty. The TCM Security courses are affordable and well-structured. Once confident, tackle OSCP to establish the industry-standard baseline. Follow with CRTP to deepen Active Directory knowledge, which is essential for nearly all internal engagements.

Timeline: 12-18 months Investment: ~$2,500-3,000

Intermediate Path

OSCP → CRTO → OSEP

For those who already have OSCP or equivalent skills, CRTO adds critical command-and-control and operational tradecraft knowledge. OSEP then builds the evasion and advanced exploitation skills needed to operate against mature defenders.

Timeline: 12-15 months Investment: ~$3,000-4,000

Advanced Path

OSEP → GXPN → Custom Research

For senior practitioners aiming at exploit development and vulnerability research. After OSEP, GXPN (via SANS SEC760) covers custom exploit writing and advanced techniques. From there, the path leads to independent research, CVE discovery, and tool development.

Timeline: 12-18 months Investment: ~$7,000+ (GXPN is expensive)

Active Directory Specialist Path

CRTP → CRTO → CRTL

A focused path for those specializing in AD environments. CRTP builds the foundation, CRTO adds operational tradecraft with Cobalt Strike, and CRTL covers team leadership and advanced operations.

Timeline: 12-15 months Investment: ~$1,300-1,500

Cloud Specialist Path

CARTE → Cloud Vendor Security Certifications

For practitioners focusing on cloud-native red teaming. CARTE covers Azure and Entra ID attacks. Follow with vendor-specific security certifications (AWS Security Specialty, Azure Security Engineer, GCP Professional Cloud Security Engineer) to understand the defensive side and identify gaps.

Timeline: 9-12 months Investment: ~$1,000-2,000


AI-Assisted Red Teaming

Artificial intelligence is fundamentally changing the offensive security landscape. Red teams that incorporate AI capabilities can operate faster and at greater scale, but the technology also introduces new ethical considerations and defensive challenges.

LLM-Powered Reconnaissance

Large language models can accelerate the reconnaissance phase by processing and correlating vast amounts of open-source intelligence. Use cases include:

  • Data correlation: Feeding collected OSINT data into LLMs to identify relationships between employees, technologies, and organizational structures
  • Report summarization: Rapidly processing SEC filings, job postings, and technical documentation to extract security-relevant information
  • Query generation: Using LLMs to craft targeted search queries for identifying exposed assets, leaked credentials, or technology stacks

Automated Phishing Content Generation

AI dramatically lowers the barrier to creating convincing phishing content:

  • Pretext development: LLMs generate contextually appropriate phishing emails tailored to specific targets based on OSINT data
  • Multilingual operations: Producing fluent phishing content in any language without needing native speakers on the team
  • Variation at scale: Generating hundreds of unique email variations to avoid signature-based detection
  • Voice cloning: AI-generated voice messages for vishing campaigns using minimal sample audio

Red teams must address these capabilities honestly in engagement reports, as adversaries are already using them. See Purple Teaming for how to incorporate AI-assisted attack findings into detection improvement.

AI for Code Review and Vulnerability Discovery

LLMs and AI-assisted tools are showing increasing capability in identifying vulnerabilities:

  • Source code analysis: LLMs can review code for common vulnerability patterns (injection, authentication flaws, logic bugs) faster than manual review
  • Fuzzer augmentation: AI-guided fuzzers that learn from coverage data to generate more effective test cases
  • Variant analysis: Given a known vulnerability, AI can identify similar patterns elsewhere in the codebase
  • Configuration review: Automated analysis of cloud configurations, Kubernetes manifests, and infrastructure-as-code for security misconfigurations

Deepfakes for Social Engineering

AI-generated deepfakes present a growing concern for social engineering:

  • Video deepfakes: Real-time face-swapping during video calls for impersonation attacks
  • Voice synthesis: Cloning executive voices for business email compromise (BEC) escalation via phone
  • Document generation: Creating convincing fake documents, badges, and credentials

Red teams are beginning to incorporate deepfake testing into social engineering assessments, though this requires explicit scoping and legal authorization.

Ethical Considerations

The use of AI in red teaming raises important ethical questions:

  • Scope boundaries: AI-generated social engineering content must be covered by the rules of engagement
  • Data handling: LLM prompts containing client data may be stored by AI providers — use local models for sensitive engagements
  • Proportionality: AI capabilities can be disproportionately effective — ensure testing remains within the spirit of the engagement goals
  • Responsible disclosure: When AI tools reveal new attack techniques, responsible disclosure practices apply

Red Teaming AI/ML Systems

As organizations deploy AI and machine learning systems, red teams must expand their scope to include these as targets. This is a rapidly growing specialization within offensive security.

Prompt Injection Attacks

Prompt injection is the most accessible attack vector against LLM-integrated applications:

  • Direct injection: Crafting inputs that override system prompts to extract sensitive data or alter behavior
  • Indirect injection: Poisoning data sources (web pages, documents, emails) that LLM applications consume
  • Multi-step injection: Chaining benign-seeming prompts that gradually shift model behavior

Model Extraction and Theft

Adversaries may attempt to steal proprietary models:

  • Query-based extraction: Systematically querying a model API to reconstruct its decision boundaries
  • Side-channel attacks: Exploiting timing, memory, or power consumption to infer model parameters
  • Training data extraction: Prompting models to reproduce memorized training data, potentially exposing sensitive information

Training Data Poisoning

Attacks targeting the model training pipeline:

  • Data injection: Introducing malicious samples into training datasets to create backdoors
  • Label flipping: Subtly altering training labels to degrade model accuracy on specific inputs
  • Gradient manipulation: Attacks targeting the training process itself in federated learning scenarios

Adversarial Examples

Crafted inputs designed to fool ML models:

  • Image perturbation: Adding imperceptible noise to images to cause misclassification
  • Text adversarial examples: Modifying text in ways invisible to humans but disruptive to NLP models
  • Physical-world attacks: Adversarial patches, stickers, or modifications that fool computer vision systems in the real world

LLM Jailbreaking as Red Team Scope

Organizations deploying LLM-based products increasingly include jailbreak testing in red team engagements. This involves attempting to bypass content filters, extract system prompts, achieve privilege escalation within the application, and access restricted functionality.

For detailed coverage of AI-specific attack methodologies, see the AI/LLM Security topic.


Breach and Attack Simulation (BAS) Platforms

BAS platforms automate the execution of attack techniques to continuously validate defensive controls. They complement but do not replace manual red teaming.

What BAS Platforms Do

BAS platforms run predefined attack scenarios against production or near-production environments to test whether defensive tools (EDR, SIEM, firewalls, email gateways) detect and respond appropriately. They map attacks to the MITRE ATT&CK framework and generate reports on detection gaps.

Platform Comparison

PlatformKey FeatureATT&CK CoverageDeploymentCost Tier
AttackIQFull ATT&CK alignment, extensive scenario libraryComprehensive (200+ techniques)Agent-based, SaaS, on-premEnterprise
SafeBreachContinuous validation with large attack playbookComprehensive (250+ techniques)Agent-based, SaaSEnterprise
Picus SecurityThreat-centric approach, real-time mitigation suggestionsBroad (180+ techniques)Agent-based, SaaSMid-market to Enterprise
CymulateImmediate threat assessment, easy deploymentBroad (170+ techniques)SaaS with lightweight agentsMid-market to Enterprise

How BAS Complements Manual Red Teaming

BAS platforms and manual red teaming serve different purposes:

  • BAS excels at: Continuous validation, regression testing, coverage measurement, and demonstrating improvement over time. BAS platforms can run thousands of atomic tests regularly.
  • Manual red teaming excels at: Creative attack chaining, novel technique development, social engineering, physical security testing, and testing human response alongside technical controls.

The most effective security programs use both. BAS provides continuous baseline validation, while periodic red team engagements test the organization against realistic, adaptive adversaries.

Limitations of BAS

  • Simulations may not trigger the same detections as real attacks due to differences in execution context
  • BAS platforms cannot test social engineering, physical security, or human decision-making
  • They follow predefined playbooks and cannot adapt creatively like human operators
  • Results can create false confidence if the platform’s test fidelity does not match real-world attack behavior

Cloud-Native Red Teaming

The shift from on-premises to cloud-first architectures has fundamentally changed red team operations. Cloud environments introduce new attack surfaces, new tooling requirements, and new constraints.

Evolution from On-Prem to Cloud-First

Traditional red team operations focused on network perimeter breach, lateral movement through Windows domains, and data exfiltration via network channels. Cloud-native environments shift the emphasis to:

  • Identity as the new perimeter: Compromising cloud credentials (access keys, OAuth tokens, service principals) replaces network-level initial access
  • API-driven attacks: Cloud resources are managed via APIs, making API key theft and abuse a primary attack vector
  • Metadata service exploitation: Cloud instance metadata services (IMDS) remain a common initial access vector (SSRF → IMDS → credential theft)
  • Cross-service pivoting: Moving between cloud services (e.g., from a compromised Lambda function to S3 buckets to IAM roles)

Cloud-Specific Tooling Maturity

The tooling ecosystem for cloud red teaming has matured significantly:

  • AWS: Pacu (automated AWS exploitation), Prowler (auditing), CloudGoat (vulnerable-by-design practice)
  • Azure: ROADtools, AADInternals, MicroBurst, AzureHound
  • GCP: GCPBucketBrute, ScoutSuite, Hayat
  • Multi-cloud: ScoutSuite, Steampipe, Cartography

Identity-Centric Attacks

In cloud environments, identity compromise is the primary objective:

  • Service principal abuse: Over-permissioned service accounts are the cloud equivalent of domain admin
  • Token theft and replay: Stealing OAuth tokens, JWTs, or temporary credentials from compromised workloads
  • Privilege escalation via IAM: Exploiting overly permissive IAM policies to escalate from low-privilege to administrative access
  • Cross-account trust abuse: Moving between AWS accounts or Azure tenants through trust relationships

Serverless and Container Attacks

  • Serverless: Exploiting function misconfigurations, environment variable secrets, overly broad execution roles, and event injection in Lambda/Azure Functions/Cloud Functions
  • Containers: Escaping container isolation, attacking the orchestration layer (Kubernetes API server), exploiting misconfigured RBAC, and accessing secrets stored in etcd
  • Supply chain: Compromising container images in registries, injecting malicious layers, and exploiting base image vulnerabilities

Zero Trust Implications for Red Teaming

Zero trust architecture (ZTA) is reshaping both defensive postures and red team operations. As organizations adopt zero trust principles, red teams must adapt their techniques and methodologies.

How Zero Trust Changes Red Team Operations

Traditional red team operations relied on the assumption that once past the perimeter, lateral movement would be relatively unconstrained. Zero trust eliminates this assumption:

  • No implicit trust: Every access request is verified regardless of source location, eliminating the value of simple network positioning
  • Microsegmentation: Network segments are granularly controlled, making traditional lateral movement techniques less effective
  • Continuous verification: Sessions are continuously validated, reducing the window for stolen credential exploitation
  • Least privilege enforcement: Users and services have minimal permissions, limiting the blast radius of any single compromise

Adapting TTPs for Zero Trust Environments

Red teams operating against zero trust architectures must evolve their approach:

Identity-Focused Attack Paths

  • Target the identity provider (IdP) itself — compromising Entra ID, Okta, or PingFederate can bypass downstream controls
  • Pursue token theft and session hijacking rather than credential harvesting
  • Exploit conditional access policy gaps (device compliance bypass, location spoofing)
  • Attack MFA implementations (MFA fatigue, adversary-in-the-middle phishing for tokens)

Microsegmentation Challenges

  • Traditional scanning and pivoting through flat networks no longer works
  • Red teams must identify allowed communication paths and work within them
  • Application-layer attacks become more important than network-layer attacks
  • Abuse of legitimate application communication channels for lateral movement

Exploiting Zero Trust Implementation Gaps

  • Zero trust implementations are rarely complete — finding the gaps is the red team’s objective
  • Legacy systems that cannot participate in zero trust architectures are high-value targets
  • Shadow IT and unmanaged devices often bypass zero trust controls
  • Monitoring and response capabilities may lag behind preventive controls

Red Team Value in Zero Trust Validation

Red team engagements become more valuable, not less, in zero trust environments. They validate whether the zero trust implementation actually works under realistic adversarial pressure. Organizations need to know whether their microsegmentation holds, whether their identity verification can be bypassed, and whether their continuous monitoring detects real attacks.


The Future of Red Teaming

Automation Augmentation, Not Replacement

The future of red teaming is not fully automated attacks replacing human operators. Instead, automation will augment human creativity and decision-making:

  • Automated reconnaissance feeds into human-driven attack planning
  • AI-suggested attack paths accelerate decision-making but require human judgment for execution
  • Automated reporting reduces the administrative burden, freeing operators for more testing time
  • Continuous monitoring tools identify changes in the target environment between engagements

Human operators remain essential for creative problem-solving, social engineering, physical security testing, and adapting to unexpected defensive responses.

AI-Human Hybrid Teams

The most effective future red teams will combine AI capabilities with human expertise:

  • AI handles repetitive tasks: scanning, enumeration, initial vulnerability identification, report drafting
  • Humans handle creative tasks: novel attack development, social engineering, physical security, strategic decision-making
  • AI provides real-time operational support: suggesting techniques, identifying patterns, correlating data during engagements
  • Humans provide quality control: validating AI-identified findings, ensuring accuracy, making judgment calls

Regulatory Expansion

Regulatory frameworks are increasingly mandating offensive security testing:

  • DORA (Digital Operational Resilience Act): Requires threat-led penetration testing (TLPT) for financial entities in the EU, building on the TIBER-EU framework
  • NIS2 (Network and Information Security Directive 2): Expands cybersecurity requirements across essential and important entities in the EU, including incident response testing
  • PCI DSS 4.0: Continues to require penetration testing with updated requirements for segmentation testing
  • SEC Cybersecurity Disclosure Rules: While not mandating red teaming directly, the disclosure requirements incentivize proactive testing

This regulatory expansion is increasing demand for qualified red team professionals and driving formalization of the discipline.

Continuous Security Validation

The model is shifting from periodic assessments to continuous validation:

  • Always-on red teaming: Persistent red team presence testing specific threat scenarios continuously
  • BAS integration: Automated attack simulation running between manual engagements
  • Purple team operations: Continuous collaboration between red and blue teams, as discussed in Purple Teaming
  • Metrics-driven programs: Measuring time-to-detect, time-to-respond, and coverage metrics continuously rather than point-in-time

Offensive Security as a Service (OSaaS)

The delivery model for red teaming is evolving:

  • Subscription-based red teaming: Organizations subscribe to ongoing red team services rather than discrete engagements
  • Platform-delivered testing: Combining automated tools with human operators through unified platforms
  • Specialized boutique services: Niche providers focusing on specific attack domains (cloud, AI/ML, IoT, OT)
  • Crowd-sourced offensive testing: Bug bounty programs expanding to include red team-style engagements

Key Takeaways

  1. Certifications are a tool, not a destination — use them strategically to build skills and demonstrate capability, but do not collect them for their own sake.

  2. Practical certifications carry the most weight — OSCP, CRTO, CRTP, and OSEP are valued because they prove hands-on ability under pressure.

  3. Build a coherent certification path aligned with your career goals, whether that is general red teaming, AD specialization, cloud, or exploit development.

  4. AI is augmenting red teams, not replacing them — learn to leverage AI tools for reconnaissance, content generation, and analysis while maintaining the creative human element.

  5. Red teaming AI systems is a growing specialization — prompt injection, model extraction, and adversarial attacks are becoming standard red team scope.

  6. BAS platforms complement but do not replace manual red teaming — use both for comprehensive security validation.

  7. Zero trust architectures require evolved TTPs — identity-focused attacks and implementation gap exploitation replace traditional network-based lateral movement.

  8. The regulatory landscape is expanding — DORA, NIS2, and similar frameworks are increasing demand for qualified red team professionals.

  9. Continuous validation is replacing periodic testing — the future is always-on security testing that combines automation with human expertise.

  10. Invest in fundamentals — regardless of emerging trends, strong foundations in networking, operating systems, and programming remain the bedrock of effective red teaming. Review Fundamentals regularly.


Further Reading

  • OffSec Training Library: Official courses for OSCP, OSEP, and related certifications
  • Zero-Point Security: Red Team Ops (CRTO) and Red Team Ops II (CRTL) courses
  • Altered Security: CRTP, CARTE, and other AD/cloud-focused training
  • SANS Offensive Operations: SEC560 (GPEN), SEC760 (GXPN), and related courses
  • TCM Security Academy: PNPT and practical beginner-friendly courses
  • MITRE ATT&CK: Framework for mapping certifications and BAS coverage to real-world techniques
  • NIST SP 800-207: Zero Trust Architecture reference for understanding what red teams are testing against