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“As custodians of digital assets, you should actually custodize assets, not outsource. Software Secured helped us prove that our custody technology truly delivers on that promise for our clients in both the cryptocurrency and traditional finance”

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Attack Chains: The Hidden Weakness in Modern API & Web Application Security

Alexis Savard
November 21, 2025
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Pentest Buyer's Guide

This guide helps SaaS and technology leaders understand how penetration testing is scoped, priced, delivered, and evaluated so they can make informed decisions when selecting a vendor.

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Key Takeaways

  • Understand the factors that influence penetration testing pricing and scope.
  • Learn how to compare vendors beyond price alone.
  • Identify the information you'll need before requesting quotes.
  • Understand the differences between annual testing, PTaaS, and continuous testing models.
  • Learn what should be included in a high-quality pentest report.
  • Discover common scoping mistakes that lead to inaccurate pricing and incomplete testing.
  • Understand how compliance requirements such as SOC 2, ISO 27001, HIPAA, and PCI DSS affect pentesting requirements.
  • Learn how to evaluate remediation support, retesting policies, and post-engagement services.
  • Get practical guidance for selecting a penetration testing partner that fits your organization's size, maturity, and security objectives.
  • Contents

      Pentest Buyer's Guide
        Software Secured

        Pentest Buyer's Guide

        Everything you need to know to select the right penetration testing partner and maximize the value of your security investment.

        17+ Questions
        Answered
        15 min read
        Comprehensive
        Expert Vetted
        Best practices

        1. Methodology & Quality

        1
        What testing methodology do you primarily follow?

        Our pentesting aligns with industry-standard frameworks including:

        • OWASP Top 10 - Critical web application security risks
        • SANS Top 25 - Most dangerous software errors
        • ASVS Level 1 - Application Security Verification Standard
        • WSTG - Web Security Testing Guide
        • NIST - National Institute of Standards and Technology

        AI pentesting aligns with MITRE ATLAS, Google SAIF, and OWASP Top 10 for ML.

        Mobile pentesting aligns with OWASP Mobile Top 10.

        Backed by industry-specific test plans, informed by active attack patterns.

        2
        What is the typical split between manual and automated testing?

        Our pentesting is ~90% manual effort. We leverage scanning tools and automation to speed our efforts and cast a wide net; however, the majority of the engagement is human-led hacking. On average, we find 26 vulnerabilities per web application pentest; 20% being critical or high.

        We conduct product demos and light threat modelling during kick-off calls to build custom attacks tailored to your business logic and data flow - this yields more severe vulnerabilities that external threat actors would find.

        3
        Do you manually validate all findings to ensure zero false positives?

        100% - we know our clients are busy and our reputation matters. All pentest reports go through QA with another pentester, and scoring is calibrated to 2 industry standards (CVSS 4.0 and DREAD) to remove any false positives and ensure quality.

        4
        What certifications do your testers typically hold?

        All testers are FTE based in Canada and are required to possess at least one of the following designations:

        OSCPOSEPGSSPGWAPTCEHCRESTCISSP

        2. Scope & Approach

        Testing Types Explained

        Black Box Testing

        Simulates an external attacker with no prior knowledge of your systems. It has the narrowest scope and is budget-friendly. Meets standard compliance requirements (SOC 2) but provides less depth and coverage.

        Gray Box Testing

        Simulates an authenticated attacker with user-level access to your application. Industry best practice for SaaS companies. Enterprise customers and partners often require this level of security because it provides deeper coverage. Recommended for most SaaS companies.

        White Box (Secure Code Review)

        Simulates an attacker with full access to your source code and architecture. Highest level of depth and visibility into risk. Recommended for companies processing PHI, operating in regulated industries, or those with mature security programs.

        6
        Which testing approach do you recommend?

        For most SaaS companies, we recommend scoping both gray box and black box tests:

        • Grey box is the industry's best practice for enterprise security requirements.
        • A black box provides an external network assessment.
        • We include an external black box network pentest with every authenticated gray box web app pentest.
        7
        How do you handle multi-site architectures?

        For architectures with multiple client-facing websites sharing the same back-end, we recommend testing a staging or testing environment of the shared back-end and a sample front-end client-facing site. Testing every site would become costly and likely produce redundant vulnerabilities.

        8
        Does testing include real-world attack chaining?

        Yes! We include a Highest Threat Summary with gray-box pentests that outlines how multiple vulnerabilities could lead to a larger issue or highlight a theme in an area of improvement for your security posture.

        We've found critical breaches by chaining together lower-severity vulnerabilities.

        3. Reporting & Remediation

        9
        What deliverables are included?
        • Executive summary - external facing for clients, partners and auditors
        • Detailed technical report - internal facing for developers, IT and security teams
        • Risk ratings with every vulnerability
        • Remediation guidance
        • Retesting (multiple rounds available based on scope)
        • Readout report meetings
        • Dedicated Slack channel for pentester communication
        • Portal dashboard for project management - custom SLAs, ticketing system integration and compliance mapping
        10
        How do reports support SOC 2 Type II evidence requirements?

        We offer one-way sync with Drata and Vanta GRC automation tools.

        Pentesting directly supports:

        • CC7.1 - Monitoring
        • CC7.2 - Vulnerability management
        • CC4.1 - Ongoing and separate evaluations

        We also map vulnerabilities to SOC 2 controls and are SOC 2 attested ourselves in addition to mapping to ISO 27001, HIPAA and PCI-DSS.

        4. Retesting Policy

        Retesting Rounds
        • Black Box: 1 round of retesting included
        • Gray Box: 3 rounds of retesting included
        • PTaaS: Unlimited retesting for biannual/quarterly/monthly clients

        Retesting is available for 6 months after report delivery. Standard SLAs: 15 days for critical, 1 month for high, 3 months for medium, 6 months for low severity.

        5. Timeline & Process

        12
        What is the typical timeline from kickoff to final report?

        Generally, we book 3-6 weeks out as we are a manual shop. Once the pentest is completed, we take 2 days for QA before shipping the final report. Need this faster? Tell us your deadline - we'll do our best to prioritize and accelerate where possible.

        If you need to change testing dates, we require at least 2 weeks' notice.

        13
        How collaborative is the process?

        You will have:

        • A dedicated pentester to work with
        • A Pentest Manager (Senior Pentester) overseeing the kick-off and support
        • Account Manager for ongoing support
        • Portal for project management

        We provide draft reports when we find critical vulnerabilities in production, allowing clients to remediate before test completion.

        Average Preparation Time

        On average, clients take 8 minutes to complete the preparation checklist in the Portal.

        6. Pricing & Engagement

        Black Box Pentest
        $5,400
        Starting price
        ✓External network testing
        ✓1 round of retesting included
        ✓~8 vulnerabilities found on average
        ✓Meets standard SOC 2 compliance
        Learn more
        Gray Box Pentest
        $10,800
        Starting price
        ✓Authenticated web app testing
        ✓3 rounds of retesting included
        ✓~26 vulnerabilities found on average
        ✓Includes external black box network test
        Industry best practice for enterprise clients and compliance
        Learn more
        15
        For subsequent engagements, do you perform full re-tests or delta testing?

        Annual pentests are full pentests on the entire app, as new CVEs are found every day and code changes over time.

        For PTaaS (more frequent than annual testing), subsequent tests focus on the delta and cost fewer days of testing once the baseline app has been pentested.

        When to Consider PTaaS

        Usual triggers to invest in more frequent pentesting:

        • Pushing so much code each sprint that annual pentests create too much risk
        • Contractual mandates from major clients
        • Recently raised funding and growing dev team faster than security
        • Want to reduce the bottleneck of annual remediation work

        Learn more about PTaaS →

        7. Crowdsourced vs Full-Time Pentesters

        When deciding between crowdsourced and full-time pentesters, it's essential to consider how each aligns with your organization's security needs, long-term goals, and budget.

        Crowdsourced Pentesters

        External cybersecurity professionals who participate in bug bounty programs or are contracted by pentesting firms. Platforms like Bugcrowd, HackerOne, and Synack connect organizations with a global pool of skilled testers.

        Full-Time Pentesters

        Cybersecurity experts employed directly or through dedicated firms. They have deeper understanding of your business logic, systems, applications, and security requirements.

        8. External Pentest vs Vulnerability Scanning

        Understanding the Difference

        The difference between external network penetration testing and vulnerability scanning is significant. Each approach has its own advantages and disadvantages, and knowing when to use each one is crucial.

        External Penetration Testing

        A security assessment that focuses on identifying and exploiting vulnerabilities in externally facing systems (websites, email servers, firewalls). Simulates an attack from an external adversary who does not have internal access.

        Vulnerability Scanning

        An automated process that identifies security weaknesses using specialized tools to scan for known vulnerabilities, misconfigurations, and outdated software, providing a detailed report.

        FeatureVulnerability ScanningPenetration Testing
        PurposeIdentify weaknessesExploit & validate
        Depth of AnalysisSurface-levelDeep analysis
        MethodologyAutomated scansManual + automated
        Skill Level RequiredLow to mediumHigh expertise
        False Positive RateHigherZero (validated)
        Business Logic TestingNoYes

        9. Testing Tools & Resources

        Below is a selection of open source and commercial tools we use in our pentesting engagements:

        Network / Infrastructure Layer
        Nmap
        Network discovery & port/service scanner for host enumeration and OS detection
        Nessus
        Commercial vulnerability scanner for network/host assessment and compliance checks
        DNSRecon
        DNS enumeration and zone/record discovery tool for domain reconnaissance
        Web Application Layer
        Burp Suite
        Full-featured web security testing proxy suite (intercepting proxy, scanner, intruder, extensions)
        ffuf
        Fast web fuzzer (directory/virtual-host/parameter fuzzing) written in Go
        wfuzz
        Web application fuzzer for bruteforcing parameters, directories and injection points
        sqlmap
        Automated SQL injection detection & exploitation tool (DB fingerprinting, data extraction)
        AppScan
        Enterprise application security scanning suite for static/dynamic/interactive app testing
        Recon / OSINT
        subfinder
        Fast passive subdomain discovery using many passive sources and APIs
        reconFTW
        Automated reconnaissance framework bundling subdomain enumeration, scans, OSINT and fuzzing
        cloud_enum
        Multi-cloud OSINT enumerator for public cloud resources (S3, storage, apps) across AWS/Azure/GCP
        BBOT
        Multipurpose OSINT/recon scanner (often used for automated recon workflows)

        10. Preparation Checklist

        Key Preparation Steps
        • Prepare staging environment with production-equivalent configuration
        • Gather IP addresses and URLs for external network testing
        • Create test accounts with appropriate role levels
        • Document any areas of concern for the security team
        • Notify relevant stakeholders about testing windows

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