Red Team Penetration Testing
A red team is simulated test to help determine whether your tools, procedures, and teams are ready for a real attack. Red teaming asks whether a determined, patient adversary could achieve a specific objective inside your organization, and whether anyone would notice before it was too late.
A guide to red teaming and how it differs from more traditional pentesting.
What is Red Team Penetration Testing?
Red team pentesting is, in short, a simulated attack against an organization and its defenses, performed by penetration testers acting the role of a threat actor. It is a controlled test, with the testers usually working to achieve specific targets. They usually occur without most of the defending security team’s knowing what’s about to happen.
Every organization runs on assumptions about what servers or applications are important, and which tools will notify them of an impending attack. During testing, the red team’s job is to find out what happens when those assumptions are wrong, then actually test them rather than debate them.
Unlike a standard pentest, which has a pre-defined and often narrow scope, red team engagements are built to test an organization’s broad response to potential threats. Red teaming as a concept is older than computers, and its core discipline has nothing to do with exploits at all: it’s a structured, adversarial challenge to an organization’s own assumptions.
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PETaaS® is on-demand pentesting services, which provides you with continuous access to our penetration testing expertise rather than a one-time assessment. This approach offers on-demand or scheduled testing, which integrates with your software development lifecycle, and delivers regular vulnerability analysis with ongoing support. While it may initially appear more expensive than traditional testing, PETaaS® is significantly more cost-effective than hiring full-time security staff and provides proactive, real-time vulnerability identification.
Note: The industry lacks a standard definition for penetration testing as a service, so verify that your provider’s approach aligns with your expectations.
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A Brief History of Red Teaming
Penetration testing has roots dating back to the 1960s with the rise of computing and digital technologies, but it gained real prominence in the 1990s as the internet became widely adopted. Red teaming as its own distinct discipline traces the same lineage, with a few milestones of its own.
- 1980s-1990s: The emergence of the Morris worm in 1988, distributed via the internet, highlighted the need for security testing and resulted in the first US conviction under the 1986 Computer Fraud and Abuse Act.
- 2000s: The Open-Source Security Testing Methodology Manual (OSSTMM) was introduced as one of the first formal frameworks to guide the information technology security community in structured security testing at an enterprise level.
- 2000s-2010: Compliance requirements, including PCI DSS, introduced the concept of regular, recurring security testing for organizations handling sensitive information, turning periodic testing into a contractual and regulatory obligation.
- 2010s: Penetration testing firmly established itself as a tool in the enterprise arsenal. Standalone pentests were the most common approach, but the rise of cloud computing and mobile technologies expanded endpoints beyond internal networks, prompting more businesses than ever to consider deeper, adversary-style testing.
- 2020s: Data breaches, ransomware, and the exploitation of zero-day vulnerabilities hammered the defenses of organizations worldwide, including the 2021 global assault on Microsoft Exchange Servers. These events pushed organizations toward more continuous, adversary-informed testing models rather than a single annual event.
- Today: Red teaming sits at the top of the security testing maturity curve, testing whether an entire organization, technology, process, and people together, can detect and withstand a determined adversary pursuing a real objective.
Secure Ideas’ own methodology is a direct product of this lineage: a cyclical, four-phase process built and refined over nearly two decades of running these engagements ourselves.
Red Team vs. Everything Else
A red team engagement is a specific and advanced type of pentesting, which could be confused with other types of pentesting. Be wary of any consulting firm using “red team” and “penetration test” interchangeably. Different types of pentesting engagements reveal different things, but if your security team is not ready for a red team, the insights from that test may not be actionable. A more mature organization will benefit more from a red team than one with a less mature security practice.
The maturity ladder
An organization’s security maturity is a strong indicator of the types of testing that organization needs. Organizations that have recently built out a security function will benefit more from more targeted pentests and vulnerability scans, which provide guidance to strengthen the baseline security. As the security function becomes more mature, they benefit more from different kinds of simulated attacks, such as adversary emulation or red teams.
Purple teaming is a collaborative companion practice that runs alongside red teaming, rather than being a step below or above it. It can help organizations get to a point where they could benefit from a red team engagement.
Threat-Informed Red Teaming and MITRE ATT&CK
The MITRE ATT&CK framework is a globally maintained knowledge base of real-world adversary behavior, built from actual observed intrusions. This is a key framework for performing red team engagements, because it gives the red team testers a repeatable methodology, as well as a common language to talk about the results of the test.
When threat intelligence relevant to a specific client’s industry and geography is available and in scope, it shapes which techniques get prioritized during an engagement.
Note that ATT&CK is a behavioral taxonomy, and not actual threat intelligence Where a Red team engagement is based more on the kinds of attack patterns that an organization could be vulnerable to. For a test grounded in real-world threat intelligence, consider a Threat Led Penetration Test (TLPT). Make sure you are clear on the kind of test you need during a scoping call.
Anatomy of a Red Team Engagement
Security consulting firms each have slightly different methodologies, which often have some broad similarities. We can’t really cover every possible red team structure, so the following section describes Secure Ideas’ methodology. The core process is a cyclical, four-phase methodology wrapped in continuous monitoring and a detection assessment.
Successful exploitation can open new territory to reconnaissance and map, cycling the process again, all while detection capability is being assessed throughout. Additionally, successful exploitation at any stage can trigger another full pass through the cycle.
PHASE 1
Reconnaissance
Before any technical action against a live system, we build a picture of the organization from public and semi-public sources. This may include employee names and roles (relevant to social engineering, if in scope), hosts and infrastructure associated with the organization, host and service configuration information visible externally, and previously disclosed vulnerabilities.
For a threat-informed engagement, this is also where cyber threat intelligence relevant to the client’s sector and geography gets incorporated. This information shapes which techniques the rest of the engagement will prioritize.
PHASE 2
System and Service Mapping
With reconnaissance data in hand, we begin studying the systems and services exposed in the target environment. We look at: network architecture and segmentation, try to determine whether it’s flat, or genuinely segmented the way it’s assumed to be. What’s exposed to the internet versus only internally, operating system and application fingerprinting. Any sensitive data visible within accessible shares and services.
Anything that doesn’t match expected patterns gets flagged as an area of interest to examine further during the test.
PHASE 3
Discovery
The team uses reconnaissance and mapping data to generate a specific list of potentially exploitable weaknesses, which they will further test using a deliberate combination of automated tooling and manual techniques. These tests include:
- Authentication, authorization, and session management: default credentials, login/registration/password-reset flaws, horizontal and vertical privilege escalation, SSO weaknesses, and Active Directory configuration issues, nearly all requiring manual testing.
- Encryption and configuration: known-vulnerable components, TLS/SSL weaknesses, and gaps in encryption-at-rest.
- Server and service exposure: known vulnerabilities tied to service versions, exploitable misconfigurations, exposed shared datastores, and potential pivot points.
- Client system and application weaknesses: exploitable client software, misconfigured endpoints, and exposure to lateral movement and credential relay-style attacks.
- Everything else: segmentation flaws, credential capture via man-in-the-middle or poisoning, social engineering opportunities created by internal exposure, and data exposure inside services a straightforward scan wouldn’t catch.
PHASE 4
Exploitation
Having tested the potential vulnerabilities, the team will then attempt to gain deeper access. The exploitation phase allows testers to confirm real-world exposure to the identified findings, and see how deep an attacker could go. Where pivoting and deeper post-exploitation are explicitly in scope, we continue from that foothold toward the engagement’s actual objective. The goal of this phase is to find out how far an attacker could get, and whether the security team and their tools can catch and stop us.
Denial-of-service conditions are never triggered without separate, explicit written permission.
THROUGHOUT
Monitoring and Detection Assessment
Across all four phases, we also attempt to determine what the organization’s actual monitoring capability looks like in practice, and at what threshold of activity the organization would detect an attack in progress, producing a real answer to how far a genuine attacker’s activity would get before anyone noticed.
How this maps to broader industry standards. The Penetration Testing Execution Standard (PTES) breaks testing into seven phases, and NIST Special Publication 800-115 uses five. Our four-phase cycle maps cleanly onto both, the substance is the same, just organized differently. What matters isn’t which framework’s phase count a report cites; it’s whether real threat modeling, genuine manual testing beyond automated scanning, and confirmed rather than assumed exploitability are actually happening.
An evaluation of your security program against the PCI Data Security Standard, covering PCI security assessments, self-assessment support, and advising on scope, applicability, and controls. You get direct access to a Qualified Security Assessor who speaks plainly and knows the standard inside and out.
Led by the “PCI Guy” himself – Jeff Man.
Attack Vectors: What a Red Team Actually Tests
Includes: Public info, employee roles, leaked stack details, exposed infrastructure, prior breach data, forms the foundation for almost everything downstream.
Includes: External and internal network testing, segmentation validation, protocol-level attacks, and lateral movement once an initial foothold is established.
Includes: Cloud applications, RESTful APIs, and web applications tested with full rigor when they provide a path toward the engagement’s objective.
Rules of Engagement, Authorization, and Deconfliction
The trusted agent
The targeted organization designates a senior stakeholder on the client side, typically the CISO or an executive sponsor, as the single point of contact who knows that the engagement is real and authorized. Their job is deconfliction: distinguishing our activity from a genuine incident in real time, without tipping off the broader organization and without leaving our team exposed if something escalates unexpectedly.
The Rules of Engagement (RoE) document
Every Secure Ideas red team engagement operates under a formal RoE that defines the exact scope, including in-scope and explicitly out-of-scope systems, networks, and physical locations, as well as permitted and prohibited techniques, testing windows, and emergency stop procedures. Because these engagements most often run covertly, our RoE accounts for scenarios that a standard pentest RoE doesn’t need to: what happens if the client’s SOC detects activity but doesn’t escalate, what happens if it escalates to an executive who is not aware of the test, and what happens if the situation escalates all the way to law enforcement.
The Letter of Authorization, often informally called a “get out of jail free” letter, is a signed, dated document proving that the engagement is authorized. This letter is carried by every team member during any activity that could otherwise look indistinguishable from a real crime. These are necessary because of cases like a well-documented 2019 case, where authorized penetration testers working a physical engagement for a state court system were arrested by a local sheriff’s deputy while attempting to gain physical access to a courthouse, despite carrying signed authorization documentation. This case is exactly why authorization must be airtight and known to the right people in advance, and not just technically valid on paper.
Prohibited actions and communication
These are usually included in the RoE document, but many red teams also define what types of testing and communication are out-of-scope. For example, Denial-of-service conditions are never exercised without separate, explicit written permission, and destructive actions or anything affecting systems or people outside the agreed scope are excluded by default.
We recommend maintaining a private communication channel between our team and the client’s trusted agent throughout the engagement, and that clients keep a whitelist of our testers’ source IP addresses internally: anything outside that whitelist gets treated as a genuine threat, test or no test, no exceptions.
What a Red Team Measures
A red team engagement is designed to test a security organization’s defenses under simulated real-world attack conditions. This allows the security team to see how their tools respond to attack traffic, how their teams respond to alerts, and close an attacker can get to achieving a goal. Where a traditional pentest identifies security gaps to be fixed, a red team engagement tests how well each part of the security organization works together.
In a 2024 advisory of a U.S. critical infrastructure organization (which was anonymized in the public report), including the team’s actual technical path. The report included the following details:
- Blocked attempt: A phishing campaign failed against a technical control that the organization didn’t even know it had.
- Reconnaissance: The red team used publicly available tools to identify an unpatched server with an XML External Entity (XXE) vulnerability, which allowed them to gain access through a web shell.
- Privilege escalation: The team gained access to an account that had unnecessary sudo rights, giving them access to all files stored in a Network File Share (NFS) device.
- ~2 weeks after initial access: The red team compromised a Windows domain controller, giving them access to all joined devices, and an Operational Technology (OT) dashboard.
The report showed that the organization’s defenses were built almost entirely around endpoint detection, with comparatively little network-level visibility. These are the kinds of structural gaps that only show up when someone tests the whole chain, rather than a single control in isolation.
The results showed a chained attack that started with an unpatched piece of software and led to full domain compromise. A vulnerability scan could surface the outdated server, but would struggle to demonstrate how far an attacker could take that attack.
Our Monitoring and Detection Assessment, built into every engagement, exists to answer that question for every client, working with the organization throughout to determine actual detection thresholds and provide recommendations grounded in what was observed, not assumed.
Why Do Red Teaming?
The Cost of Getting It Wrong
Security breaches are becoming more common, and they carry financial and reputational costs. IBM’s 2025 Cost of a Data Breach Report found the global average was $4.44 million, and the U.S. average rose to $10.22 million, which is an all-time high. Healthcare was identified as the most expensive sector for the 14th straight year at $7.42 million. If a breach includes customer data, this can lead to a loss of consumer confidence, which can carry its own long-term impacts.
Regulations Requiring Red Teaming
As cybersecurity regulations evolve, formal requirements for testing like Red Teaming become more prevalent. For example, the EU’s DORA regulation requires Threat-Led Penetration Testing for significant financial entities. The regulation mandates real threat intelligence, a genuine red team, and a purple team debrief. The U.S. is trending similarly across PCI DSS, GLBA, and evolving HIPAA guidance.
The Impacts of Chained Attacks
Real intrusions rarely come from a single, isolated exploit. Chained attacks could allow an attacker to gain initial access through one overlooked gap, move laterally through another vulnerability, and then escalate privilege by exploiting a third. Where a traditional pentest identifies individual vulnerabilities, a red team engagement can provide a picture of how an attacker could chain multiple issues together to provide deeper access.
Board and Insurer Documentation
Environments change as new code is deployed, new devices are attached, and new users get connected. Cyber insurance companies and executive boards are more frequently asking for regular updates on incident preparedness, while a point-in-time annual pentest drifts away from the current configuration. [Callout] CONTINUOUS TESTING – Navigating compliance requirements?
CONTINUOUS TESTING
See how PETaaS® supports continuous testing with flexible, credits-based penetration testing and built-in advisory services.
Engagement Models and Scoping
Scopes for red teams depend on organizational size and complexity, there is no flat rate for them. Larger organizations have larger attack surfaces, and require comprehensive coverage test thoroughly. Prices are calculated based on estimated effort and a daily rate. Secure Ideas uses the same consulting-day model across our other services, with a premium of around 10% of overall cost) for required off-hours work like an overnight physical break-in attempt.
For organizations that want red team-informed testing built into an ongoing cadence, our testing credit model, delivered through Professionally Evil Testing as a Service (PETaaS®), lets an organization purchase credits up front and draw on them over a 24-month window through a self-scoping system.
Risks and How They're Managed
System Outages
Sometimes a system less robust than anticipated, or a tool interacts with it in an unanticipated way, and this leads to a system or network shutting down. Secure Ideas mitigates this risk by staffing the test with experienced testers who understand the actual systems being tested, and perform controlled testing of any unfamiliar tool before production use. We also conduct active monitoring so tooling can be halted at the first sign of trouble.
Inadvertent Exposure
Perhaps backdoor gets left unprotected, or sensitive data gets transmitted insecurely during testing. This is usually accidental, or can come from missing security controls. We address this with direct supervision of junior consultants and regular, substantive communication with clients about what’s been found and targeted.
Masking of Real Attacks
Occasionally, red teaming will coincide by chance with a threat actor attempting to gain access. If a SOC disregards all of the alerts generated during a testing window, this creates a window for a genuine, unrelated attacker to operate undetected. This is exactly why we use a trusted-agent and IP-whitelisting model: anything outside the known-tester list can be treated as a real threat.
Lost Productivity
Some interference with normal operations is normal. During scoping, we can minimize this impact by informing the teams most likely to be affected and giving them a reporting channel. This gives them a way to reach out to us directly in the event something impacts their work.
False Negatives
A red team engagement is time-boxed and adversarial, and is not a comprehensive audit. This means that the testers are following the path of least resistance in the same the way a real attacker would. A red teamer may not test an otherwise valid vulnerability because of the time or techniques it would require to exploit. This is why we recommend pairing red team engagements with other assessment types over time rather than relying on any single engagement type to be exhaustive.
Vendor Quality and Trust
There is no universal license that automatically holds every tester accountable, and different people with different backgrounds may find different vulnerabilities on different days. We provide our team with the best tools and training that we can offer, and our CREST accreditation validates our testers at the organizational level.
We welcome direct questions about our consultants’ experience, background check practices, and subcontracting.
Who Actually Needs Red Teaming ?
Not every organization needs a red team engagement. They work best for organizations that fall into the following categories:
Certain industrial regulations require strong cybersecurity testing. This includes Financial services, healthcare, critical infrastructure, and any organization facing or anticipating threat-led testing requirements.
How Secure Ideas Approaches Red Teaming
Secure Ideas builds every red team engagement around a genuine four-phase, cyclical methodology, as described above. Our CREST-accredited consultants understand the systems they’re testing, not just the tools used to attack them, matching the depth this level of engagement actually requires.
Every engagement runs under a formal Rules of Engagement document and a designated trusted agent, with deconfliction procedures established before testing begins, not improvised mid-engagement. Coverage spans network, web application, cloud, social engineering, and physical vectors as scoped, evaluated as an interconnected system rather than isolated checkboxes.
We also have a built-in Monitoring and Detection Assessment that runs throughout every engagement, producing a real answer to how the organization’s actual detection capability performed, not just a list of exploited vulnerabilities. Engagements are offered in 30, 60, and 90-day models, reflecting the reality that meaningful adversary testing takes sustained time, not a single scheduled week.
Beyond the Test
Building Continuous Resilience
A red team engagement is a powerful exercise, but it’s typically run once, over a defined 30-, 60-, or 90-day window. The adversaries your organization faces don’t pause between engagements.
Building continuous resilience requires ongoing testing and advisory support between red team cycles. Regular penetration testing of applications, networks, and infrastructure ensures that new vulnerabilities are caught as your environment changes. Advisory services provide guidance on remediation priorities, architectural decisions, and emerging threats specific to your industry.
This is what Secure Ideas’ PETaaS® (Professionally Evil Testing as a Service) is designed for. PETaaS® provides continuous, human-led penetration testing through a flexible credits-based model, with built-in advisory services and real-time communication. Between red team cycles, PETaaS® keeps your testing program active and your team informed.
Think of a red team engagement as the full-scale drill that happens periodically. PETaaS® is the ongoing conditioning that keeps your defenses ready in between.
Red
Teaming
Frequently
Asked
Questions
Have a question that isn’t answered here?
See our full FAQ page.
How is red teaming different from a penetration test, in one sentence?
Where pentest determines whether a specific system has exploitable vulnerabilities, a red team engagement asks whether a real adversary could achieve a specific objective across the whole organization, undetected.
Will our own security team know the test is happening?
Generally no, and that’s intentional. Often, only a small trusted agent group, typically the CISO or an executive sponsor, is informed. The value of the engagement depends on testing genuine, and works best with unrehearsed detection and response.
Does red teaming include physical security testing?
It can, depending on the scope. Physical engagements carry unique legal and coordination requirements, including a documented letter of authorization and careful boundaries around confrontation, which are all covered explicitly in the Rules of Engagement before any testing begins.
How long does a red team engagement actually take?
We offer 30-, 60-, and 90-day models. Active testing is typically compressed into a month or less, with about a week for reporting. These time frames balance operational realism against the need to act on results in a reasonable timeframe.
Can red teaming satisfy DORA's Threat-Led Penetration Testing requirement?
Red teaming is the underlying discipline that Threat-Led Penetration Testing (TLPT) is built on, but TLPT has specific regulatory requirements, including named threat intelligence providers, specific reporting formats, a mandatory purple team phase. Some of these requirements go beyond a standard red team engagement.
Is red teaming worth it if we've never had a standard pentest?
Usually not. Red teaming gets the most value when foundational controls and monitoring are already in place to be tested. Organizations earlier in their security maturity typically get more immediate value from a standard pentest or security assessment first, as they give more practical advice for building up those foundational controls.
What does a red team engagement actually cost?
This depends on a variety of factors. Pricing is based on estimated effort and daily consulting rate, scaled to organizational size and attack surface, with a premium for required off-hours testing. Reach out for a scoping conversation specific to your environment.
Can we see a sample report from a Penetration Test?
Absolutely. Any reputable penetration testing company should provide sample reports upon request. Reports are your primary deliverable and should include an executive summary, testing narrative, detailed findings with risk ratings, replication steps for verification, and actionable remediation recommendations. Not all reports are created equal, so reviewing samples helps ensure the format and content meet your needs. Most companies will accommodate reasonable modifications to reporting formats.
What is Professionally Evil Testing as a Service (PETaaS®)?
PETaaS® is on-demand pentesting services, which provides you with continuous access to our penetration testing expertise rather than a one-time assessment. This approach offers on-demand or scheduled testing, which integrates with your software development lifecycle, and delivers regular vulnerability analysis with ongoing support. While it may initially appear more expensive than traditional testing, PETaaS® is significantly more cost-effective than hiring full-time security staff and provides proactive, real-time vulnerability identification.
Note: The industry lacks a standard definition for penetration testing as a service, so verify that your provider’s approach aligns with your expectations.
Other Pentesting Approaches
Continuous Penetration Testing
Continuous Pentesting keeps testing running instead of leaving your network exposed between annual checkups. We pair ongoing vulnerability scanning with a real consultant reviewing the results, and catching new risks as they appear across web apps, APIs, and IoT ecosystems. Regular reporting means you always know what’s new, what has changed, and where to point the roadmap next.
Security that doesn’t wait for next year’s test.
Threat-Led Penetration Testing
Threat-Led Pentesting simulates the specific tactics, techniques, and procedures of the threat actors most likely to target your organization, instead of following a generic playbook. We work with you to identify relevant adversaries and scenarios, then build a bespoke test around them. It’s the approach DORA now mandates for certain financial entities, and happens to be a strong fit for any mature security program.
Tested against the threats actually coming for you.
Purple Team Penetration Testing
Purple Team Pentesting engagements put our red team and your blue team on the same call, testing and defending in real time. As we run attacks, your team watches, tunes detection, and learns what an actual intrusion might look like on your systems. It’s a faster way to validate specific controls and walk away with sharper monitoring.
Your defenders, tested and trained at the same time.
Ride Along Penetration Testing
Ride Along Pentesting embeds our consultants directly with your internal security team, working side-by-side instead of independently. Your team gets a front-row seat to our techniques and methodology, letting them pick up skills in real time as the engagement unfolds. It’s a hands-on way to level up your team while still getting a full assessment.
Testing that trains your team while it runs.
Time-Boxed Penetration Testing
Time-Boxed Pentesting focuses effort on your highest-priority assets within a set window, instead of trying to cover everything at once. It’s a strong fit for large environments, budget-conscious teams, or anyone just getting started with testing. We work to set the scope through a quick scoping call, so the timeframe fits your risk profile, instead of a generic template.
Focused coverage, built to fit your timeline.
Recognized authority and trusted guidance built on years of uncovering risks for organizations like yours.
