Penetration testing

What is Continuous Automated Red Teaming

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Organizations invest in red teaming to mimic adversarial attacks. While red teaming exercises are essential to protecting your digital assets, annual or periodic tests are no longer enough. Continuous evaluation is now necessary to proactively strengthen systems before malicious actors can exploit vulnerabilities.

Continuous Automated Red Teaming (CART) is software that runs all the time to mimic attackers automatically across your live systems, finding attack paths and chained exploits at scale. This 24/7 monitoring reduces human error and delivers immediate threat mitigation. 

How Does Continuous Automated Red Teaming Work?

CART works by executing automated attack scenarios that mimic the techniques used by real-world threat actors. Here’s a step-by-step overview of how it works:

  1. Defining Objectives: Security teams set testing goals, such as assessing endpoint security, network defenses, or application vulnerabilities.

  2. Developing Playbooks: Automated attack playbooks are created using known TTPs to ensure scenarios are realistic.

  3. Continuous Execution: The system runs attacks repeatedly and continuously across the organization’s IT environment.

  4. Monitoring and Analysis: AI and analytics tools evaluate the results in real time, identifying vulnerabilities and gaps in detection and response.

  5. Reporting and Remediation: Actionable insights are delivered to security teams in the form of reports, enabling quick remediation before threats can be exploited.

Continuous Automated Red Teaming differs from other traditional methods by offering ongoing, real-time testing that replicates the tactics, techniques, and procedures (TTPs) of actual attackers. This allows organizations to evaluate their security more thoroughly and respond quickly to threats.

Drawbacks of Traditional Red Teaming

Manual red teaming is valuable, but it has its limitations that organizations should understand when deciding how to balance it with continuous or automated approaches.

Limited Coverage

Traditional red-teaming is expensive and scheduled infrequently, so many attack paths remain untested between exercises. New vulnerabilities, misconfigurations, or changes introduced after the test can remain undetected for long periods.

High Cost and Resource Intensity

Skilled red teams require budget, time, and specialist personnel. Complex engagements also consume engineering and ops time. Smaller organizations often cannot afford a realistic scope, and large programs can strain internal teams.

Scalability Issues

Manual tests are hard to scale and difficult to reproduce exactly, which complicates trend analysis over time. Measuring improvement or the impact of remediations becomes noisy and inconsistent.

Knowledge Transfer and Operationalizing Findings

Red teams often deliver dense technical reports that aren’t easily actionable by developers or business owners. Findings may therefore be deprioritized or misinterpreted, so root causes stay unaddressed.

Risk of Disruption and Safety Concerns

Live intrusive tests can lead to outages, data exposure, or performance issues when run in production environments. These risks can disrupt business operations, increase privacy concerns, and trigger resistance from engineering teams.

Dependence on Individual Skills and Methods

Results can vary depending on the red team’s creativity, tooling, and personnel. Two teams might produce very different coverage. 

Slow Feedback-to-Remediation 

Manual reports sometimes arrive weeks after exercises, and remediation can take months. Vulnerabilities remain exploitable, and the situational context can be lost.

Compliance/Legal Constraints

Regulations or contractual obligations can limit what testers are allowed to do, especially with production or customer data.

The Benefits of Continuous Automated Red Teaming

CART provides numerous advantages over traditional approaches:

  1. 24/7 Threat Emulation: Continuous red teaming ensures that vulnerabilities are detected as they happen.

  2. Reduced Human Error: Automation ensures consistent and repeatable attack simulations.

  3. Scalability: Large and complex IT environments can be tested simultaneously without additional human resources.

  4. Immediate Threat Mitigation: Real-time insights enable faster remediation of security gaps.

  5. Better Risk Management: Security teams can prioritize vulnerabilities based on severity and likelihood of exploitation.

  6. Improved Compliance: Continuous monitoring can support regulatory requirements such as ISO 27001, GDPR, and NIST frameworks.

  7. Actionable Analytics: Advanced reporting and dashboards provide visibility into security posture and improvement over time.

Common Pitfalls in Continuous Red Teaming

Continuous red teaming offers great coverage and repeatability, but it also introduces specific risks if not run carefully. Below are the most common pitfalls with practical ways to avoid them:

  1. Over‑reliance on automation: Automation increases scale but misses creative adversary behavior, unexpected privilege escalations, or business‑logic flaws.

    How to avoid: Balance automation with periodic human-led red-team engagements. Triage high‑severity automated findings with experienced testers before large remediation campaigns.

  2. Alert fatigue and noise: Low‑value or duplicate findings flood SOC queues and reduce trust in CART outputs.

    How to avoid: Tune thresholds and severity mappings, suppress known false positives, and add contextual enrichment.

  3. Testing without business context: Tests focus on technical exploits that have little real impact on business priorities.

    How to avoid: Use risk‑based scoping. Prioritize crown jewels (IDs, payments, IP) and map findings to business impact and remediation cost for sensible prioritisation.

  4. Poor scoping or runaway tests: Tests run too broadly or invasively, causing outages, data exposure, or operational disruption.

    How to avoid: Enforce strict rules of engagement, time‑box tests, use limited credentials, prefer staging for destructive scenarios, and include automated rollbacks or kill switches.

  5. Weak integration with ticketing and remediation workflows: Findings sit in reports and never translate to fixes.

    How to avoid: Integrate CART with ITSM/SOAR to auto-create actionable tickets, attach repro steps, assign owners, and verify remediation via re‑scans.

  6. Stale attack playbooks and intelligence: Playbooks become outdated and miss current attacker TTPs.

    How to avoid: Version control playbooks, schedule regular reviews driven by threat intelligence, and automate feed updates where sensible.

    7. Lack of cross‑team ownership: CART results are siloed in security and ignored by engineering or business teams.

    How to avoid: Create governance with stakeholders from security, engineering, and business; feed findings into sprint backlogs and require remediation sign‑offs.

    8. Misaligned KPIs: Metrics focus on activity rather than impact.

    How to avoid: Track outcome-focused KPIs, including time-to-containment for simulated attacks, telemetry-based detection coverage, and the reduction of high-severity findings over time.

What Types of Attacks can CART Simulate?

CART can emulate a wide range of adversary behaviors to continuously validate detection and response. Common, high-value simulations include:

Reconnaissance: port/subdomain scans and OSINT

Credential attacks
: phishing, password spraying, credential stuffing

Web/API attacks:
  XSS, SQL injection, and parameter tampering are common; use automated tests and web application scanning to find and fix them.

Exploitation and privilege escalation
: proof-of-concept CVE exploits and lateral movement.

C2 and exfiltration emulation
: beaconing, DNS tunnelling, staged data export.

Cloud/IAM abuse
: misconfigurations and role misuse.

Supply-chain / CI-pipeline abuse
: malicious pipeline changes or package tampering.

Multi-stage attack chains: end-to-end scenarios combining the above. 

Keep simulations non-destructive and map each play to the telemetry you expect to capture; that’s how CART turns tests into measurable improvements.

Best Practices for Continuous Automated Red Teaming

Adopt these best practices to get the most from Continuous Automated Red Teaming (CART). All designed to ensure CART delivers continuous, actionable improvements to your security posture without disrupting operations.

Integrate CART with Your Security Stack

  • API-first integrations: Connect CART to vulnerability scanners via APIs so findings and telemetry flow automatically into existing workflows.

  • Event correlation: Make sure CART-generated events are mapped to the same event taxonomy used by your SIEM so analysts can correlate attacks with other alerts.

  • Automated play triggers: Use vulnerability management outputs to drive CART scenarios automatically.

  • Feedback loop into patching: Feed confirmed findings to workflows so remediation becomes an automatic next step, not a manual handoff.

Prioritize Attack Surfaces

  • Asset classification: Keep an up-to-date inventory that tags assets by business impact and exposure.

  • Risk-based scenario selection: Run CART more frequently against internet-facing services, identity systems, and systems that process sensitive data. Lower-frequency sweeps are fine for low-impact assets. For a deeper understanding of how to identify and prioritize exposures, see our guide on attack surface management.

Keep Attack Playbooks Updated

  • Threat‑intel updates: Link playbooks to current threat actors and revise them when new campaigns or tools appear.

  • Versioning & reviews: Schedule regular reviews (e.g., monthly or after major intel) and keep changelogs with reasons for each update.

Establish Clear, Measurable Metrics

  • Key performance indicators: E.g-mean time to detect (MTTD) and mean time to remediate (MTTR)

  • Outcome-focused metrics: Measure time-to-containment during simulations, reduction in detection gaps, and closure of high-severity findings within SLA.

  • Reporting & dashboards: Provide executive dashboards for high-level trends and detailed dashboards for operators showing step-by-step actions and remediation tasks. Say goodbye to spreadsheets and manual tracking by using the Rootshell platform.

Collaborate across Teams 

  • Cross-functional governance: Create a CART steering group with representatives from security ops, engineering, DevOps, application owners, and business stakeholders to approve scope, SLAs, and risk tolerances.

  • Embed in development lifecycle: Integrate CART findings into sprint backlogs and CI/CD pipelines so developers fix the root causes, not just symptoms.

  • Purple team sessions: Run regular purple-team exercises where CART results are reviewed in real time with the Security Operations Center (SOC) and engineering teams to refine detection rules and response playbooks.

Validate Automated Findings with Human Review

  • Triage process: Put a human analyst in the loop for high-severity or ambiguous findings.

  • Periodic manual red-team audits: Schedule quarterly or semi-annual manual red-team audits to validate CART’s coverage

  • Sampling & external reviews: Randomly sample automated findings for deeper manual validation and complement them with external vulnerability scanning to get an objective view.

Comparing CART to Other Security Methods

The table below compares four common security assessment approaches across frequency, level of automation, scope, primary advantage, and main limitation. Use it to quickly see which method suits your organization’s needs for depth, scale, and operational integration.

Security Method

Frequency

Automation

Scope

Key Advantage

Key Limitation

Traditional Red Teaming

Periodic 

Manual

Limited to selected systems

Realistic expert testing

Expensive, slow, gaps between tests

Vulnerability Scanning

Continuous or periodic

Automated

Broad

Quick identification of known vulnerabilities

Cannot emulate attacker behavior

Penetration Testing

Periodic

Manual

Focused

Deep assessment of specific systems

Slow, costly, limited coverage

CART

Continuous

Automated

Enterprisewide

Real-time threat simulation, scalable, actionable insights

Requires integration and maintenance

How CART Differs from Traditional Pen Testing

Continuous Automated Red Teaming (CART) and traditional penetration testing (BAS) both aim to uncover vulnerabilities, but they differ in scope and approach. Traditional pen tests are typically manual and periodic, providing a snapshot of security at a specific moment. CART, on the other hand, runs continuously and automatically, simulating attacker behavior across systems to identify weaknesses as they arise. This constant testing also helps validate whether security controls and detection mechanisms are working in real time.

Unlike traditional tests, which rely heavily on human effort to explore attack paths and provide post-assessment recommendations, CART uses automation to scale across complex environments. It allows organisations to repeatedly test scenarios without the time and resource constraints of manual testing. 

Implementing CART in Your Organization

Implementing Continuous Automated Red Teaming (CART) requires careful planning to ensure it delivers actionable insights without disrupting operations. The following steps guide organizations through selecting the right solution, developing realistic playbooks, integrating with existing security workflows, and training teams to respond effectively.

  1. Assess Current Security Posture: Identify gaps and critical assets.

  2. Select the Right CART Solution: Evaluate tools based on automation, AI capabilities, integration, and reporting features.

  3. Develop Playbooks: Create realistic attack scenarios aligned with your threat model.

  4. Integrate with Security Operations: Ensure alerts feed into SIEM and SOC workflows.

  5. Monitor and Refine: Continuously evaluate results, update playbooks, and improve detection and response.

  6. Train Staff: Ensure IT and security teams understand insights and remediation procedures.

Continuous Automated Red Teaming (CART) moves organizations from episodic, resource‑heavy testing to continuous, measurable security validation. CART helps you find and fix attack paths faster, reduce risk, and improve detection and response over time.

When You Should Use a Red Team

Engaging a red team is appropriate when you need to test people, processes, and detection capabilities under pressure. Red teaming is most valuable when your organization wants to validate its incident response or assess the effectiveness of security controls in a live environment.

Consider commissioning a red team exercise if any of the following apply:

  • You are protecting high-value assets and need assurance beyond routine vulnerability scans.

  • You have recently changed architecture, adopted cloud-native services, or deployed new identity/privilege models, and want to test how those changes look to an attacker.

  • You have matured your standard security testing (DAST, pen tests) and need a step up to full-scope, real‑world attack simulations.

  • You are preparing for a regulatory audit, cyber insurance assessment, or board-level review and need demonstrable evidence of real-world resilience.

  • You want to validate your detection and response playbooks, run book handoffs, and cross-team coordination under simulated attack conditions.

A red team engagement should be planned when stakeholders can act on findings. Define clear objectives, scope, success criteria, and rules of engagement in advance, and ensure incident response teams are briefed. Done well, red teaming exposes systemic weaknesses, prioritizes remediation by real risk, and strengthens your organization’s ability to detect, respond, and recover from attacks.

How Continuous Automated Red Teaming Benefits Your Business

Continuous Automated Red Teaming (CART) provides ongoing, realistic simulations of attacker behavior. Unlike periodic tests, CART continuously identifies vulnerabilities and exposure points, allowing organisations to address weaknesses before they can be exploited. This proactive approach reduces risk and ensures that security measures are working in real time.

CART also improves operational efficiency by automating routine testing and monitoring, freeing security teams to focus on analysing results and improving detection and response capabilities. Book a demo to see how Rootshell operationalises CART and simplifies vulnerability management. 

Frequently Asked Questions

Can’t find the answer to your question?
You can always Contact Our Team of experts for a chat!

Is Red Teaming illegal?

Red teaming is not illegal when it is conducted with proper authorization. Organizations hire red teams to simulate attacks on their own systems, networks, or applications to identify vulnerabilities and improve security. Problems arise only if someone performs red team activities without consent, targeting systems they do not own or have explicit permission to test, which would be considered illegal hacking.

Many tasks can be automated for continuous coverage, but humans are still needed for creative attack chaining, social engineering, and complex business‑logic abuse.

Tip: Use a hybrid approach: automated continuous testing plus periodic human red‑team engagements.

Costs vary widely by vendor, scope, and scale. Budget components include licensing, integration work, playbook development, engineering time for remediation, and periodic human red-team validation. Consider the total cost of ownership against the cost of undetected breaches and compliance fines.

In the context of artificial intelligence (AI), red teaming refers to the process of deliberately testing an AI system to identify weaknesses, vulnerabilities, or unintended behaviors before they can be exploited or cause harm. Experts (or automated systems) act like “attackers” to challenge the AI model’s safety and reliability.

Pink teaming is a collaborative cybersecurity approach that combines elements of both red teaming (offensive testing) and blue teaming (defensive monitoring and response). Instead of operating in opposition. 

While traditional red vs. blue exercises are adversarial,  with red teams simulating attackers and blue teams defending, pink teaming emphasizes cooperation, communication, and shared learning.

Picture of Shaun Peapell
Shaun Peapell
Shaun Peapell is the Vice President of Global Threat Services at Rootshell Security, leading efforts in penetration testing and threat intelligence. He is actively involved in industry discussions on continuous testing methodologies.​

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