Top 10 Questions to Ask Your Penetration Testing Vendor
- arunprasad160
- Mar 16
- 4 min read
Updated: Mar 30
So, you have built a great SaaS App!! But what about its security?
There are a wide range of penetration testing vendors with the potential to drain your pockets either through quick and cheap service or through lengthy, complex and expensive audits, with no way to determine which one provides the best services and leaving you in a vulnerable and confused state.
Fear not, for we've compiled a set of practical questions to assist you in your quest.
Can you identify vulnerabilities that automated scanners missed?
Whereas a mediocre vendor will start talking about SQL injection findings, an elite vendor will describe how they found a critical flaw by understanding how your industry works. They'll explain their process of discovering vulnerabilities in places where automated tools don't even know to look — business logic/ process flaws, hidden data combinations, and rare conditions that only appear under specific circumstances.
The best vendors demonstrate their expertise through detailed technical explanations, sharing their methodology and showing how they combined technical expertise with business understanding to uncover critical vulnerabilities that could have devastated their clients' operations.
What security research has your team published?
A vendor who isn't actively contributing to security research isn't learning from it either.
The security landscape transforms daily as new attack techniques emerge; novel vulnerabilities are discovered.
Elite security teams don't just keep up — they drive the industry forward through open-source tool contributions, and detailed technical analyses of new attack techniques.
The best security partners are those who advance the collective knowledge of the security community to improving cybersecurity standards.
Can you walk me through your approach to testing serverless architectures?
Modern SaaS platforms are complex systems. Serverless functions, microservices, and cloud-native architectures bring security challenges.
An expert penetration testing provider will detail function timeout exploitation techniques, event injection methodologies, serverless permission evaluation, and cloud configuration assessment. They should explain how their testing adapts to service mesh architectures and modern deployment patterns.
The right vendor demonstrates a deep understanding of testing methodologies specifically designed for modern architectures.
What is your process for validating findings and ensuring accuracy?
This question cuts through marketing talk and gets to the heart of testing quality. A vendor's validation process reveals their commitment to accuracy and thoroughness. If they can't describe their validation process in detail, it is likely they don't have one. This raises serious questions about the reliability of their findings.
Elite vendors maintain rigorous validation protocols. They articulate their multi-stage verification process, including how they document proof-of-concepts for complex vulnerabilities. Their approach includes peer review systems and transparent methodologies for confirming findings before reporting them.
Can you demonstrate custom tools and novel testing techniques?
The best security teams develop their own tools and techniques because commercial tools often fall short. Their custom solutions should demonstrate a deep understanding of modern application security challenges. They should be able to describe their specialized testing frameworks, custom fuzzing engines, and unique exploitation tools.
Penetration testing vendors should demonstrate and explain why they developed bespoke tools — what gaps in commercial solutions they address and how they improve testing effectiveness.
How do you align penetration testing for our industry vertical?
Generic testing methodologies miss context-specific vulnerabilities. The right vendor demonstrates a deep understanding of your industry's unique security challenges and regulatory requirements.They should explain their approach to identifying industry-specific attack scenarios, understanding regulatory compliance implications for your industry and how they align their penetration testing approach for this.
Their methodology should show precise adaptation to your industry's particular risks and requirements.
What is your approach to testing in CI/CD pipelines?
Modern SaaS platforms deploy continuously. Traditional point-in-time testing no longer suffices. Elite vendors understand this fundamental shift in development practices. Their response should detail their API-first testing approach, their strategy for handling rate limiting, and their methods for integrating security testing into rapid deployment cycles.
Penetration testing vendors with real world practical experience will explain how they maintain testing effectiveness without becoming a bottleneck in your development process.
How do you assess our entire attack surface, including forgotten assets?
Your attack surface extends beyond your known assets. Forgotten systems and shadow IT often provide attackers with an initial foothold. The right vendor employs sophisticated asset discovery methods. They should describe their passive reconnaissance techniques, certificate transparency monitoring, and cloud resource discovery methods.
Their approach should demonstrate how they find and assess assets you might not even know exist.
What is your process for testing third-party integrations?
Modern SaaS platforms often rely heavily on third-party services and integrations. Each integration point represents a potential vulnerability. Elite vendors should detail their methodology for testing API integrations, analyzing OAuth flows, and assessing third-party dependencies.
They should explain how they evaluate supply chain risks and test the security of your platform's interactions with external services.
How do you support the development team in implementing fixes?
Finding vulnerabilities is only half the battle. Elite vendors understand that their real value comes from helping you implement effective fixes. They should offer developer consultation sessions, provide detailed remediation guidance, and assist with fix verification.
Their support should extend from beyond merely pointing out problems, to helping your team understand and address root causes.
Beyond the Questions
The vendors who can give clear, detailed answers to these questions are the ones who understand this reality. They're the ones who will treat your application's security with the seriousness it deserves. The right vendor will ask as many questions as they answer. They should inquire about your development practices, deployment processes, business priorities, and risk tolerance. Their questions reveal their commitment to understanding your specific security needs.
Making Your Decision
Your choice of penetration testing vendor will influence your applications security posture and journey. Selecting the right penetration testing vendor is a crucial step in your journey.
Use these questions as your guide but also trust your instincts – if something feels off about a vendor's responses, it probably is.
Your platform's security deserves more than checkbox compliance and automated scans.
Click here to download a comprehensive E-Book covering the top 10 questions for your penetration testing vendor with a vendor scoring sheet that will guide you through the process of choosing a vendor who is best aligned to protect your organization
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