RA-5(9): Penetration Testing and Analyses

RA-5(9): Penetration Testing and Analyses requires you to plan, authorize, execute, and document penetration testing and follow-on analysis as part of your vulnerability management program, then track remediation to validated closure. Operationalize it by setting a testing scope and cadence, using qualified testers, producing an executive and technical report, and keeping an auditable evidence bundle tied to system risk. ¹

Key takeaways:

• Treat pen testing as a governed control with scope, rules of engagement, approvals, and evidence, not an ad hoc security exercise.
• Your “pass/fail” is auditability plus remediation closure: documented findings, prioritization, retest, and sign-off.
• Define triggers (major changes, new exposures, incident learnings) so testing happens when risk changes, not only on a calendar.

If you’re a CCO, GRC lead, or compliance officer supporting federal systems or contractor environments, RA-5(9): penetration testing and analyses is one of the fastest ways auditors test whether your vulnerability management program is real. They will look for more than a penetration test report. They will ask who approved it, what was in scope, what constraints existed, how you prevented business disruption, how you handled high-risk findings, and whether you validated fixes.

Operationalizing RA-5(9) means turning penetration testing into a repeatable, authorized process with clear ownership, defined triggers, and a minimum evidence bundle. The work splits cleanly into two tracks: (1) governance (scope, rules, approvals, independence, and safety controls) and (2) execution (testing, analysis, reporting, remediation, retest, closure). Your goal is a defensible story that connects pen testing to your system risk posture and produces tangible risk reduction.

This page gives requirement-level implementation guidance you can use immediately: who it applies to, what to do step-by-step, what artifacts to retain, common audit hangups, and a practical execution plan.

Requirement: ra-5(9): penetration testing and analyses requirement (plain-English)

RA-5(9) expects you to perform penetration testing and analyze results as part of your vulnerability identification and remediation practices. In plain terms: you must intentionally simulate realistic attacks against your system (within agreed rules), document what was possible, determine root causes and control gaps, and drive fixes to verified closure. ¹

The “analyses” portion is where programs often fail. Auditors and customers expect you to translate findings into:

• affected assets and business processes
• exploited conditions (misconfigurations, missing controls, insecure design paths)
• compensating controls (if you cannot fix immediately)
• a prioritized remediation plan with owners and deadlines
• retest evidence that fixes worked

Regulatory text

Excerpt: “NIST SP 800-53 control RA-5.9.” ¹

What an operator must do: Treat penetration testing as a defined enhancement within your RA-5 vulnerability monitoring program. Document how you decide when to run penetration tests, what you test, who is authorized to approve testing, how you analyze outcomes, and how you ensure findings are remediated and validated. ¹

Authoritative sources for the control definition and context:

• NIST SP 800-53 Rev. 5 OSCAL JSON ¹
• NIST SP 800-53 Rev. 5 landing page ²

Who it applies to

Entity types (typical applicability):

• Federal information systems
• Contractor systems handling federal data ¹

Operational context:
RA-5(9) becomes “in scope” when you operate systems where NIST SP 800-53 is a contractual, regulatory, or assurance baseline (for example, an ATO boundary, a federal enclave, or an environment processing federal information). It also commonly appears as a customer due diligence requirement for third parties that host, process, or secure government-related workloads.

What you actually need to do (step-by-step)

Below is a practical runbook you can assign to an owner and audit quickly.

1) Create a control card (owner, triggers, boundaries)

Document a one-page “control card” that answers:

• Control owner: named role (e.g., Head of Offensive Security or Vulnerability Management Lead)
• In-scope systems: ATO boundary, environments, critical apps, external attack surface
• Triggers: major releases, architecture changes, new internet exposure, identity changes, material incidents, and scheduled cadence
• Success criteria: report delivered, remediation plan approved, retest complete, risk accepted by the right authority when needed

This addresses the most common gap: teams can’t show who owns the requirement, how often it runs, or which evidence proves it is operating. ¹

2) Define the penetration testing standard and rules of engagement (RoE)

Write (or update) a Rules of Engagement document that includes:

• authorized targets (hostnames/IP ranges, apps, APIs, cloud accounts)
• authorized methods (black/gray/white box, social engineering allowed or prohibited, phishing rules if permitted)
• constraints (no production data exfiltration, rate limits, time windows, no persistence)
• safety controls (backups confirmed, monitoring enabled, emergency stop contacts)
• evidence handling (how sensitive proof is stored, who can view it)
• legal/contractual authorization (internal approval plus any required third-party approvals)

Operational note: this RoE is your “permission slip” in an exam. Without it, the best test report still looks like an uncontrolled activity.

3) Set tester qualifications and independence expectations

Define whether testing is performed by:

• an internal team independent of the build/ops team, or
• a qualified external third party

What auditors typically want to see is credible independence and competence for the scope. Capture this as a selection memo or SOW statement, then retain resumes/certifications or a capability statement as appropriate.

4) Build a realistic scope and test plan tied to risk

Create a test plan that maps to your threat model and architecture:

• external perimeter and internet-facing services
• identity paths (SSO, privileged access, service accounts)
• segmentation and lateral movement paths
• cloud control plane and misconfiguration paths
• high-risk business functions (payments, claims, benefits, sensitive datasets)

Include explicit out-of-scope items and why (e.g., legacy system pending decommission). Then document compensating controls or interim monitoring.

5) Obtain approvals and schedule safely

Before testing starts, collect:

• system owner approval
• change management notice (if required)
• SOC/IR notification procedures (avoid false incident escalation)
• third-party approvals for hosted/SaaS components when you are not the system owner

6) Execute testing and capture defensible evidence

During execution, ensure testers capture:

• steps to reproduce (commands, payloads, screenshots)
• affected assets, user roles, and privileges required
• impact narrative aligned to confidentiality/integrity/availability
• proof that exploitation was possible within RoE constraints

Do not accept a report that only lists scanner outputs. Pen testing should show exploit paths and chained weaknesses where relevant.

7) Perform “analyses” and translate into engineering actions

Run a structured findings review with Security, Engineering, and the System Owner:

• root cause (process gap, design flaw, missing hardening, IAM misconfiguration)
• control mapping (which preventive/detective controls failed)
• fix approach (config, code, architecture)
• priority and due date
• decision: remediate, mitigate, or formally accept risk

If a finding cannot be fixed quickly, require a documented compensating control and risk acceptance from an authorized risk owner.

8) Track remediation to validated closure (with retest)

Create tickets for each finding and track:

• owner
• target date
• deployment evidence (PR links, change records, config diffs)
• retest evidence (internal retest notes or third-party verification)

Closure means retested, not “engineer says done.”

9) Report up and preserve the evidence bundle

Deliver two outputs:

• Executive summary: themes, systemic issues, risk posture change, and any accepted risks
• Technical report: detailed findings and reproduction steps

Store them in a controlled repository with access restrictions.

Required evidence and artifacts to retain (minimum bundle)

Use this checklist to be audit-ready:

Artifact	What auditors look for	Owner
Control card / runbook	Named owner, cadence/triggers, scope boundaries	GRC + Security
Rules of Engagement	Authorized targets/methods, safety controls, stop contacts	Security
Test plan & scope statement	Risk-based scope, in/out scope, assumptions	Security + System Owner
Approval records	System owner authorization, third-party permissions	GRC / System Owner
Final pen test report(s)	Findings quality, evidence, impact narratives	Testing lead
Findings register	Unique IDs, severity rationale, status, owners	Vulnerability Mgmt
Remediation tickets & change evidence	Traceability from finding to fix	Engineering
Retest/validation evidence	Proof fixes worked	Security
Risk acceptance memos (if any)	Authorized sign-off, expiration/review date	Risk owner

A practical control health check is to confirm each completed test has this full bundle and that closure is documented, not implied. ¹

Common exam/audit questions and hangups

Expect these questions verbatim in many assessments:

• “Show me the last penetration test for this system boundary and who approved it.”
• “What was in scope and why? What was explicitly out of scope?”
• “How do you ensure testing is safe in production?”
• “How do you prioritize findings, and who can accept risk?”
• “Show evidence of retest and closure for the highest-risk findings.”
• “What triggers an off-cycle pen test after major changes?”

Hangup patterns:

• No retest evidence. The remediation story ends at “ticket closed.”
• Unclear authorization. No RoE, no system owner approval, or approvals buried in email without a durable record.
• Scope mismatch. Testing ignores the actual attack surface (new APIs, cloud control plane, identity flows).

Frequent implementation mistakes (and how to avoid them)

1. Treating a vulnerability scan as a pen test.
   Fix: require exploit narratives, chain demonstrations (where safe), and reproduction steps.

2. Running a pen test with no operational guardrails.
   Fix: RoE with explicit safety constraints, monitoring coordination, and stop authority.

3. No analysis beyond “patch X.”
   Fix: add root-cause categories and control failures; create systemic remediation epics where patterns exist.

4. Letting third-party test reports live in inboxes.
   Fix: central repository with controlled access, retention, and linkage to the findings register.

5. Risk acceptance without authority.
   Fix: define who can accept risk for a system and require signed memos tied to findings, with review triggers.

Enforcement context and risk implications

No public enforcement cases were provided in your source catalog for RA-5(9). Treat this as an assurance and contractual risk: failure typically shows up as audit findings, ATO delays, customer security exceptions, or contractual noncompliance in third-party assessments. ¹

Practical implication: RA-5(9) gaps tend to cascade. If you cannot prove pen testing is governed and repeatable, assessors often question adjacent areas: change control, vulnerability management, incident response readiness, and risk acceptance discipline.

Practical execution plan (30/60/90-day)

Use phases instead of date promises. Fit them to your release cycle and assessment calendar.

Immediate (stabilize governance)

• Assign a single control owner and backups.
• Draft the control card and minimum evidence bundle checklist.
• Inventory in-scope systems and confirm the current attack surface (domains, apps, cloud accounts, APIs).
• Draft/update Rules of Engagement and an approval workflow (ticket, memo, or GRC system).

Near-term (execute and produce evidence)

• Select the testing team (internal independent or external third party) and document selection rationale.
• Build a risk-based scope and test plan for the highest-risk system boundary first.
• Run the penetration test, deliver executive + technical reports, and log findings in a register.
• Start remediation tickets with clear owners and due dates.

Ongoing (operationalize and prove closure)

• Run retests for remediated items and attach validation evidence.
• Hold a recurring findings review with Security and Engineering to drive root-cause fixes.
• Perform periodic control health checks: verify each cycle has the complete evidence bundle and that exceptions have documented approval. ¹

Where Daydream fits (earned mention)

If your biggest friction is audit-ready evidence, Daydream can standardize the RA-5(9) control card, enforce the minimum evidence bundle per test cycle, and track remediation items to validated closure so you can answer audits with a single linked record instead of scattered documents. ¹

Frequently Asked Questions

Do we have to hire an external third party to meet RA-5(9)?

NIST SP 800-53 does not require an external firm in the excerpt provided. You do need credible governance, documented authorization, and defensible results analysis and remediation closure. ¹

How often do we need to run penetration tests?

The source excerpt does not specify a frequency. Define a cadence and off-cycle triggers tied to risk and material change, then document and follow them consistently. ¹

Can we test in production?

Yes, many teams do, but only with a clear Rules of Engagement, safety constraints, and coordination with operations and incident response. Auditors typically focus on authorization, risk controls, and evidence of controlled execution. ¹

What evidence is most critical for auditors?

Approvals (system owner authorization), defined scope/RoE, the final report, a findings register, and proof of remediation with retest evidence. Missing retest evidence is a common failure point. ¹

What if we cannot remediate a finding before an audit?

Document compensating controls and a formal risk acceptance by the right risk owner, tied to the specific finding, with a planned remediation path or review trigger. Keep that memo with the test evidence bundle. ¹

How do we handle findings that affect a hosted SaaS where we can’t change the underlying platform?

Document shared responsibility, push remediation actions that are available to you (configuration, identity controls, monitoring), and track the remainder as third-party risk with escalation and contractual follow-up where possible. Keep the correspondence and decisions as part of the analysis record. ¹

Footnotes

1. NIST SP 800-53 Rev. 5 OSCAL JSON

2. NIST SP 800-53 Rev. 5