Penetration testing should make your organisation more secure. If you're reading dense reports with no clear action plan, waiting months for testing to begin, or watching vulnerabilities persist long after testing ends, something has gone wrong.
The problem isn't penetration testing itself but how the industry delivers it. Too many providers treat testing as a product rather than a partnership. They scope engagements to satisfy procurement rather than address real risks. They deliver reports instead of results.
In our guide to penetration testing, we explored what effective security testing should look like, from smart scoping and context-aware methodologies to collaborative execution and meaningful reporting.
However, understanding what good testing entails is only half the equation. The other half is knowing how to find and work with providers who can actually deliver it.
This second chapter bridges that gap. We'll show you how to identify quality providers, structure effective engagements, and ensure you get measurable security improvements, not just compliance checkboxes.
Hidden costs of ineffective penetration testing
Before describing what good penetration testing looks like, let's examine why so many engagements fail to deliver value. Understanding these hidden costs helps you avoid them.
Hidden cost #1. The compliance trap
Many organisations approach penetration testing as a necessary evil, something required by auditors or regulations rather than a strategic security investment. This mindset leads to procurement processes focused on cost rather than capability, scope documents that limit effectiveness, and success metrics that measure completion rather than improvement.
"While we've traditionally viewed pen testing as a process to find system flaws and ensure security, I believe we've lost our way, allowing a compliance-driven mindset to overshadow the true spirit of cyber security," points out penetration testing expert Dan Haagman.
The real cost: You spend money on testing that satisfies paperwork requirements but leaves critical vulnerabilities unaddressed. Your security posture remains unchanged, but your budget is depleted.
Hidden cost #2. The lead time tax
Traditional penetration testing models involve lengthy procurement cycles, detailed scoping exercises, and scheduling windows that stretch weeks or months into the future. While this might work for annual compliance exercises, it fails in dynamic environments where infrastructure changes continuously.
The real cost: Delayed security validation means vulnerable systems go live, creating exposure windows that attackers can exploit. When it finally happens, the testing may no longer reflect production reality.
Hidden cost #3. The report graveyard
How many penetration testing reports are gathering dust on servers? The industry has developed an addiction to comprehensive documentation that serves audit trails better than security teams. These reports often contain:
Dozens of findings with no clear prioritisation
Technical details that developers can't action
Remediation advice that doesn't fit your environment
Executive summaries that fail to communicate business risk
The real cost: Security teams waste time trying to make sense of findings while critical vulnerabilities remain unpatched. The effort required to translate reports into action often exceeds the effort to fix the underlying issues.
Hidden cost #4. The disappearing act
Perhaps the most frustrating aspect of traditional penetration testing is what happens after report delivery. Many providers consider their job complete once findings are documented. But this is precisely when organisations need the most support: turning discoveries into security improvements.
The real cost: Without remediation guidance, retesting support, and ongoing consultation, vulnerabilities persist indefinitely. Organisations pay for discovery but not resolution.
Red flags: Six warning signs of poor providers
Certain behaviours and approaches signal providers who are unlikely to deliver real value. Watch for these warning signs during your evaluation process:
Red flag #1. Generic scope templates
If a provider presents you with a standard scope document that could apply to any organisation, they haven't invested time understanding your specific risks and priorities.
"The scope problem becomes evident when we see organisations with well-secured applications but vulnerable single sign-on systems. Providers often look in the wrong places, focusing on narrow scopes that miss the broader attack surface," explains Dan Haagman.
Quality providers customise their approach based on your environment, threats, and objectives.
Red flag #2. Reluctance to explain methodology
Providers who can't clearly explain their testing approach, tools, or techniques either lack depth or are hiding behind proprietary claims.
Effective penetration testing isn't magic. It's a methodical process that should be transparent and understandable.
Red flag #3. Focus on tool capabilities over human expertise
While tools are important, penetration testing value comes from human insight, contextual analysis, and creative problem-solving.
Providers who emphasise their scanning capabilities over their team's expertise are likely to deliver automated vulnerability assessments rather than meaningful security validation.
Jacob Thampi, VP and Divisional Information Security Officer at QBE North America, shared a personal experience highlighting this problem:
"I remember early on running a security assessment tool and receiving a third-party report that was an exact copy of the tool's output."
Red flag #4. Rigid scope adherence
Pen testing providers who refuse to adjust the scope based on discoveries during testing miss opportunities to explore critical attack paths.
Good penetration testing requires flexibility to pursue meaningful findings even if they weren't anticipated in the original scope.
Red flag #5. Limited post-delivery support
If a provider's engagement ends with report delivery, they're selling documentation rather than security improvement.
"What we often see is that security service providers will come in, generate a report — be it seventy-two, eighty-five pages, doesn't matter — and that's it. The whole engagement is very transactional: here's your templated report, thank you for your business, and we're done," says Joel Earnshaw, senior manager of cyber security.
Quality pen testing providers support remediation efforts and verify that fixes actually work.
Red flag #6. Unrealistic pricing or timelines
Effective penetration testing requires skilled professionals, time for thorough analysis, and comprehensive documentation.
Prices significantly below market rates or unrealistically short timelines often indicate:
Junior testers lacking the necessary expertise
Rushed testing with insufficient time for thorough analysis
Generic reporting with minimal customisation
Limited or no post-engagement support
Corner-cutting that reduces testing quality and value
What quality penetration testing looks like
Understanding common failure scenarios helps, but what should you expect from effective penetration testing? Here are the characteristics that separate valuable engagements from expensive exercises:
Context-driven scoping
Quality providers begin with your business objectives, not their standard scope templates. They ask about:
Critical business processes and data
Existing security controls and compensating measures
Recent infrastructure changes or upcoming deployments
Specific threat concerns based on your industry or profile
Internal team capabilities and resource constraints
This context shapes everything from testing methodology to reporting format. A financial institution faces different risks than a manufacturing company, and testing should reflect those differences.
Jacob Thampi emphasises this in our article about why generic pen testing falls short:
"We need to deliver pen testing with context. While compliance is a major driver, simply providing the output without that context isn't sufficient."
Joel Earnshaw agrees:
"You must have an understanding or appreciation of what's important to the business. What's mission critical? What can we do without? When you have that context around what's important, you can target it and get the most effective outcomes."
Transparent methodology
Effective providers clearly explain their approach, tools, and techniques. You should understand:
How they plan to test your specific environment
What techniques they'll use and why
How they'll validate findings and avoid false positives
What evidence they'll provide for each discovery
How they'll minimise the impact on production systems
Transparency builds trust and enables informed decision-making throughout the engagement, as Joel Earnshaw points out:
"To really get the best results for everyone involved, you've got to build a genuine partnership. That means being totally open and honest with each other, having complete transparency, and really understanding what matters to both sides. Without that openness and shared understanding, how can you ever expect to achieve those meaningful outcomes?"
Collaborative execution
The best penetration tests feel like joint operations rather than external audits. This means:
Regular communication during testing, not radio silence
Interim findings shared as they're discovered
Flexibility to adjust the scope based on initial discoveries
Clear escalation procedures for critical vulnerabilities
Integration with your existing security and IT processes
Active involvement of your Security Operations Centre (SOC) and IT teams throughout the engagement
Quality providers recognise that your internal teams are invaluable partners in effective testing. Your SOC and IT teams provide critical context that external testers simply cannot access:
Real-time threat — Your SOC understands current attack patterns targeting your organisation and can guide testing toward the most relevant scenarios.
Contextual vulnerabilities — Your IT teams know which systems are business-critical, how they interconnect, and what compensating controls exist.
Rapid response — Internal teams can enable immediate response to critical findings, reducing time to remediation from weeks to hours.
As cyber security strategy consultant Kevin O'Sullivan points out, "The collaborative model results in a triangle of value between the security provider, the internal security team, and the security objectives — focusing everyone on outcomes rather than outputs."
Experienced cyber security leader Robin Fewster agrees:
"A more flexible and integrated approach to pen testing would allow security consultants to work more closely with internal teams to understand their unique security needs and deliver more meaningful results."
Actionable reporting
Quality reports focus on outcomes, not just outputs. They provide:
Clear prioritisation based on business impact and exploitability
Specific remediation guidance tailored to your environment
Executive summaries that communicate effectively to business stakeholders
Technical details that developers can immediately act upon
Efficient pen testing providers offer dynamic reporting alternatives that integrate directly into your existing tools and processes.
Workflow integration — Findings delivered through platforms you already use, such as Jira, Azure DevOps, ServiceNow, or whatever your teams prefer.
Native environment — Vulnerabilities tracked within your data protection boundaries and existing project structures.
Immediate action — Issues become tickets that can be prioritised, assigned, and tracked like any other work item.
Real-time collaboration — Direct communication through your preferred channels, such as Slack or Teams.
This approach eliminates the gap between "finding" and "fixing." Your development teams don't need to interpret external reports, they get actionable tickets in their familiar environment.
Zero lead times
The traditional "we're busy" mentality of providers signals a misalignment of priorities. When providers wear their busy schedules as badges of honour, they focus on themselves rather than on security needs.
Quality providers structure their operations differently. They maintain capacity for rapid response and prioritise immediate action over procurement convenience. The best engagements begin within hours or days of agreement, not weeks or months later.
Look for pen testing providers who can:
Onboard new clients immediately when urgency demands it.
Begin testing within hours for existing clients with established relationships.
Offer rapid retesting and fix verification without additional procurement cycles.
Maintain operational flexibility that serves your timelines, not theirs.
Ongoing support
Responsiveness should extend beyond initial testing to the entire relationship. The same provider who can start testing tomorrow should be able to retest fixes next week and validate new deployments as they occur.
Effective providers support you through the entire security improvement process:
Remediation guidance and consultation
Fix verification and retesting
Knowledge transfer to internal teams
Integration with ongoing security programs
Long-term relationship rather than transactional engagement
This ongoing support, which is an essential part of our pen testing 2.0 philosophy, ensures that discoveries become security improvements.
30 questions for evaluating pen testing providers
Provider evaluation shouldn't be taken lightly, but it shouldn't overwhelm you either.
Think beyond individual engagements. You want a pen testing vendor who understands your environment, learns your priorities, and builds on previous work rather than treating each test as an isolated project.
Here's a comprehensive list of questions to help you cover your bases and identify providers capable of that kind of cyber security partnership:
Question set #1. Experience and expertise
What specific experience do you have in our industry?
Who will actually perform our testing? (Not just who will manage it)
Can you provide examples of similar engagements and their outcomes?
What certifications and training do your testing staff maintain?
How are you adapting your testing approaches to address AI-powered attacks and new threat vectors?
Question set #2. Methodology and approach
How do you customise testing methodology for different environments?
What's your process for handling critical findings during testing?
How do you validate findings and minimise false positives?
What evidence do you provide for identified vulnerabilities?
How do you ensure testing doesn't impact production systems?
How do you involve our SOC and IT teams in the testing process?
How do you handle decisions like Web Application Firewall (WAF) configuration during testing?
A sophisticated provider should discuss tactical decisions that affect testing quality and collaborate with you to make these decisions based on your testing objectives, rather than making assumptions or following rigid procedures.
Question set #3. Delivery and communication
What's your typical timeline from contract to testing completion?
How do you communicate progress and findings during engagements?
What format do your reports take, and how are they customised?
How do you prioritise findings for remediation?
What post-delivery support do you provide?
Question set #4. Quality and assurance
What's your process for quality assurance and report review?
How do you handle situations where the initial scope proves inadequate?
What guarantees or assurances do you provide regarding your work?
Can you provide client references for similar engagements?
Question set #5. Value and outcomes
How do you measure the success of penetration testing engagements?
How do you support remediation efforts after testing?
What's your approach to retesting and fixing verification?
How do you help organisations improve their overall security posture?
Question set #6. Budget and investment
What exactly is included in your quoted price?
What additional costs might we encounter during or after testing?
How do you handle scope changes or unexpected discoveries?
What ongoing support is included versus charged separately?
What's your policy on retesting after remediation?
How to structure effective engagements
Even with the right provider, engagement structure significantly impacts outcomes. Here's how to set up penetration testing for success.
Define clear objectives
Before discussing scope or methodology, clarify what you want to achieve:
Validate specific security controls or architectures
Assess exposure from particular attack scenarios
Support compliance requirements with meaningful security validation
Build internal security knowledge and capabilities
Test incident response and detection capabilities
Clear objectives guide everything else and provide success criteria for the engagement.
Embrace flexible scoping
Rather than rigid asset lists, structure the scope around:
Business-critical systems and processes
Key attack scenarios and threat models
Recent changes or new deployments
Areas of particular concern or uncertainty
Integration points and trust boundaries
This approach ensures testing focuses on what matters most while allowing flexibility to pursue important discoveries.
Plan for collaboration
Structure the engagement to enable ongoing collaboration:
Schedule regular check-ins during testing
Identify key stakeholders and their availability
Establish communication channels and escalation procedures
Plan for interim findings sharing and discussion
Integrate testing timelines with your operational schedules
Collaboration accelerates remediation and builds internal knowledge.
Integrate with existing processes
Connect penetration testing with your broader security program:
Align timing with development cycles or change windows
Integrate findings with existing vulnerability management processes
Connect testing outcomes with security metrics and reporting
Plan for knowledge transfer to internal security teams
Structure testing to support ongoing security initiatives
Integration ensures testing contributes to continuous security improvement rather than isolated point-in-time assessment.
Budget for real value
One of the most common questions buyers ask is: "What should we expect to pay for quality penetration testing?" The answer depends on several factors, such as scope and complexity, expertise level, and engagement model.
Traditional project-based: Higher per-engagement costs but limited ongoing value.
Retainer-based relationships: Lower per-test costs with continuous access and support.
Continuous testing programs: Most cost-effective for organisations with frequent changes.
What's often not included in initial quotes and can double your cost if not planned for upfront:
Remediation consultation and support
Retesting after fixes are implemented
Emergency support for critical findings
Integration with your existing tools and workflows
Executive briefings and stakeholder communication
When comparing different pen testing offers, consider these important factors:
Risk reduction value — Cost of testing versus potential breach costs.
Efficiency gains — Faster remediation through better reporting and support.
Compliance benefits — Meeting regulatory requirements effectively.
Knowledge transfer — Building internal security capabilities.
Long-term partnership — Reduced procurement overhead and compounding value.
Remember: penetration testing is insurance against cyber attacks. The goal isn't to minimise cost but to maximise security value within reasonable budget constraints.
Measure real value and cyber security ROI
How do you know if penetration testing is delivering value? Below is a checklist of outcome-based metrics to focus on, rather than on vanity measurements.
Security posture improvement
Reduction in critical and high-risk vulnerabilities over time
Decreased time to identify and remediate security issues
Improved security control effectiveness and coverage
Enhanced detection and response capabilities
Better security awareness and practices among development teams
Operational efficiency
Faster remediation cycles through better prioritisation
Reduced false positives and security noise
More effective allocation of security resources
Better alignment between security activities and business objectives
Risk reduction
Measurable decrease in exploitable attack surface
Validation of security architecture and control effectiveness
Improved confidence in security posture and risk management
Better preparation for compliance audits and assessments
Enhanced ability to respond to emerging threats
Knowledge and capability building
Increased internal security expertise and awareness
Better understanding of the threat landscape and attack techniques
Improved security processes and procedures
Enhanced collaboration between security, IT, and development teams
Stronger security culture and risk awareness across the organisation
Key takeaways for improved pen testing engagements
If you want to do testing more efficiently in your organisation, we recommend the following:
Structure contracts around outcomes, not activities. Stop paying for testing hours or report pages. Instead, structure agreements around security improvements and risk reduction outcomes. The best providers welcome accountability for results, not just deliverables.
Embrace continuous engagement over annual cycles. Replace yearly testing windows with on-demand or continuous testing that aligns with your development and operational cadences. Security validation should happen when you need it, not when the calendar says so.
Build long-term partnerships, not vendor relationships. Invest in pen testing providers who want to understand your environment deeply and improve it continuously. These partnerships eliminate repeated procurement cycles and create compounding value as vendors learn your systems and priorities.
Integrate testing with your broader security program. Look for providers who offer integrated service delivery, connecting penetration testing with vulnerability management, architecture reviews, and ongoing security consulting.
Prioritise knowledge transfer and capability building. Use each engagement as an opportunity to strengthen internal security knowledge. The best providers leave your team better equipped to identify and address security issues independently.
Demand workflow integration. Ensure pen testing providers can deliver findings through your existing tools and processes. If they can't integrate with your Jira or development workflows, they're creating friction instead of removing it.
Measure what matters. Track meaningful metrics that demonstrate security improvement: faster remediation cycles, reduced critical vulnerabilities, improved detection capabilities. Compliance metrics are necessary but insufficient.
Start with strategy, execute with flexibility. Align testing with business objectives and security strategy, but maintain flexibility to adjust scope and priorities as new information emerges. Rigid engagements miss opportunities, while adaptive ones create value.
Focus on remediation from the beginning. Budget for and plan remediation support as part of the initial engagement. Testing without fixing is expensive. Ensure your provider supports you through the entire improvement process.
Choose providers who adapt to your timeline, not theirs. Work with pen testing vendors who can start when you need it — hours or days, not weeks or months. Responsiveness reflects priorities: are they focused on your security needs or their operational convenience?
The approaches outlined in this buyer's guide to pen testing represent a different way of thinking about security testing, one focused on outcomes rather than outputs, partnership rather than transactions, and continuous improvement rather than point-in-time assessment.
If you want to see this approach in practice, read our penetration testing case study, which shows how the Chaleit team cut remediation costs by 50%, among other significant outcomes.
The bottom line: when done right, penetration testing becomes a strategic capability that strengthens your entire security program. When done wrong, it's an expensive exercise that satisfies audit requirements while leaving real risks unaddressed.
The choice is yours. We hope this guide ensures your investment in penetration testing delivers the security improvements your organisation needs and deserves.
Read next: In chapter 3, we explore the technical evolution required to move beyond traditional vulnerability-focused testing toward context-aware security validation: Modern Penetration Testing Methodology
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