Blackbox CISO Operational Security Pack

Contents

How to Use This Pack	4

Purpose	4

How to Approach the Assessment	4

How to Interpret Your Results	4

Areas of Strength	4

Visibility Gaps	4

Operational Risk Areas	4

Recommended Use	5

Important Note	5

About BlackBox Pentesters	5

1.	BlackBox Pentesters Penetration Test Buyer’s Checklist	6

Provider Capability	6

Testing Methodology	6

Scope & Coverage	6

Reporting Quality	7

Retesting & Validation	7

Operational Maturity	7

2.	BlackBox Pentesters Ransomware Readiness Snapshot	8

Backup Resilience	8

Identity Security	8

Detection Capability	8

3.	BlackBox Pentesters Attack Surface Visibility Checklist	9

Domain & External Footprint	9

Exposed Services	9

Cloud & SaaS Assets	9

4.	BlackBox Pentesters Security Logging & Visibility Gap Review	10

Identity Logging	10

Endpoint Visibility	10

Network Monitoring	10

5.	BlackBox Pentesters Red Team Readiness Assessment	11

Detection Maturity	11

Response Capability	11

Operational Readiness	11

How to Use This Pack

Why This Pack Exists

Most organisations have security controls. Far fewer have a clear understanding of how those controls perform under real-world attack conditions.

Security is often measured through compliance, tooling coverage, or completed assessments. However, breaches occur when attackers exploit visibility gaps, identity weaknesses, and operational blind spots that exist between those controls.

The BlackBox Pentesters CISO Operational Security Pack has been developed based on real-world penetration testing and red team engagements. It is designed to help you quickly identify the conditions that attackers rely on to gain access, move undetected, and achieve their objectives.

This pack provides a structured, operational view of your security readiness.

How to Use This Assessment

Each section focuses on a critical component of operational security:

Penetration testing effectiveness and provider capability

Ransomware resilience and recovery readiness

External attack surface visibility

Security logging and detection capability

Organisational readiness to detect and respond to attack

Answer each question based on your organisation’s current, verifiable state, not assumed coverage or intended future improvements.

This assessment is most effective when completed by those responsible for security operations, infrastructure, identity management, and incident response.

Accuracy is essential. Overestimating capability creates risk by masking exposure.

How to Interpret Your Results

This pack is designed to help you identify conditions that directly influence breach likelihood and impact.

Unchecked items may indicate:

Security controls that exist but lack operational visibility

Exposure that is not actively monitored or understood

Detection gaps that may allow attacker activity to persist undetected

Operational weaknesses that could delay or prevent effective response

These conditions are commonly observed during real-world compromise simulations.

The objective is not to achieve a perfect score, but to clearly understand where risk exists and where improvement will have the greatest impact.

What This Pack Helps You Achieve

This pack supports informed, risk-driven security decision-making. It can be used to:

Identify genuine operational security gaps

Validate whether existing controls provide real protection

Support security investment prioritisation

Prepare for penetration testing or red team engagements

Strengthen organisational readiness for real-world attack scenarios

Provide structured insight for executive and board-level discussions

It also provides a repeatable baseline to measure improvement over time.

Important Context

Security posture is defined by operational effectiveness, not by the number of tools deployed or assessments completed.

Attackers do not follow compliance frameworks. They exploit what is exposed, misconfigured, or unmonitored.

Understanding where those conditions exist is the first step in reducing risk.

About BlackBox Pentesters

BlackBox Pentesters is a specialist penetration testing and red team provider focused on delivering realistic security assessments aligned with real attacker behaviour.

Our work supports organisations in identifying genuine exposure, validating defensive capability, and strengthening operational resilience.

This pack reflects the same principles applied during our client engagements.

BlackBox Pentesters Penetration Test Buyer’s Checklist

Purpose: Help organisations distinguish meaningful security testing from commodity scanning

Provider Capability

Penetration testing quality is determined more by the people delivering it than the tools being used. This section exists to help organisations understand who is actually testing their environment and whether they have the experience to identify real-world attack paths rather than surface-level issues.

High-quality providers rely on experienced, full-time testers who specialise in offensive security and understand how attackers chain weaknesses together. Heavy reliance on automation, junior testers, or subcontractors often results in reports that look busy but fail to identify genuine risk.

Use the questions below to validate the provider’s depth, focus, and credibility.

Are tests conducted manually, or primarily automated?	☐
What is the tester seniority level?	☐
Are testers full-time employees or subcontractors?	☐
Does the provider specialise in security testing?	☐

Testing Methodology

A penetration test should simulate how an attacker would actually operate, not just list isolated vulnerabilities. This section helps assess whether testing is structured, repeatable, and aligned to recognised standards, while still allowing tester creativity.

Strong methodology includes exploitation validation, attack path demonstration, and business logic testing. Weak methodology tends to stop at vulnerability discovery without proving impact.

Is testing aligned to recognised frameworks (e.g. OWASP, PTES, NIST)?	☐
Is exploitation validated or just identified?	☐
Are attack paths demonstrated?	☐
Are business logic flaws assessed?	☐

Scope & Coverage

Security weaknesses rarely exist in isolation. This section ensures testing reflects how modern environments are actually breached, through identity, cloud, APIs, and misconfigurations rather than single systems.

Incomplete scope is one of the most common reasons organisations believe they are secure when they are not.

Are internal, external, and application layers included?	☐
Is identity testing performed (Active Directory / privilege paths)?	☐
Are APIs assessed where relevant? Are cloud environments in scope?	☐

Reporting Quality

A penetration test only delivers value if its findings can be understood and acted upon. This section focuses on whether reports communicate risk in business terms and support decision-making at both technical and executive levels.

Strong reporting prioritises clarity, impact, and remediation. Weak reporting overwhelms readers with raw data and little context.

Are findings risk-ranked in business context?	☐
Are exploitation narratives included?	☐
Is remediation guidance practical and prioritised?	☐
Are executive summaries board-ready?	☐

Retesting & Validation

Fixing vulnerabilities without validating the fix creates a false sense of security. This section confirms whether remediation efforts are genuinely effective, not just cosmetically addressed.

Is remediation retesting included?	☐
Are fixes validated beyond surface level?	☐
Is evidence provided for closure?	☐

Operational Maturity

Penetration testing should contribute to long-term security improvement, not just point-in-time assurance. This section assesses whether the provider can support organisations beyond delivery of a report.

Does the provider offer advisory guidance?	☐
Can they support remediation discussions?	☐
Do they provide maturity improvement recommendations?	☐

BlackBox Pentesters Ransomware Readiness Snapshot

Purpose: Quickly assess exposure to the most likely high-impact attack scenario

Backup Resilience

Ransomware resilience depends on whether backups are protected from compromise and usable during recovery. This section evaluates separation, testing, and survivability of backup systems.

Are backups segregated from domain access?	☐
Are backups tested regularly?	☐
Is offline backup maintained?	☐

Identity Security

Identity is the primary attack vector for ransomware operators. Weak privileged account controls often enable rapid domain-wide compromise.

Are privileged accounts monitored?	☐
Is MFA enforced for admins?	☐
Are service accounts reviewed?	☐

Detection Capability

Early detection can significantly reduce ransomware impact. This section assesses whether behaviours associated with ransomware activity are visible and actionable.

Is unusual encryption activity monitored?	☐
Are lateral movement alerts configured?	☐
Is SOC coverage 24/7?	☐

BlackBox Pentesters Attack Surface Visibility Checklist

Purpose: Identify unknown, unmanaged, or forgotten exposure

Domain & External Footprint

Organisations are frequently breached through assets they no longer track. This section helps establish whether the external footprint is fully understood.

Have all corporate domains been identified?	☐
Are subdomains continuously monitored?	☐
Are legacy domains still active?	☐

Exposed Services

Internet-facing services are prime targets. This section assesses whether exposure is intentional, controlled, and monitored.

Are internet-facing services inventoried?	☐
Is remote access restricted appropriately?	☐
Are administrative interfaces exposed?	☐

Cloud & SaaS Assets

Cloud and SaaS sprawl often introduces hidden risk. This section ensures visibility across modern platforms and integrations.

Are cloud environments asset-tracked?	☐
Are storage buckets exposure-reviewed?	☐
Are SaaS integrations risk assessed?	☐

BlackBox Pentesters Security Logging & Visibility Gap Review

Purpose: Determine whether attacks can be detected and investigated

Identity Logging

Identity logs are critical for detecting compromise and tracing attacker movement.

Are authentication logs centrally stored	☐
Are privilege escalations monitored?	☐
Is anomalous login detection configured?	☐

Endpoint Visibility

Endpoints are where attackers execute actions. This section evaluates whether malicious behaviour can be observed and investigated.

Is EDR deployed across all endpoints?	☐
Are suspicious processes logged?	☐
Is USB/device activity monitored?	☐

Network Monitoring

Network visibility supports detection of lateral movement and data exfiltration.

Is east-west traffic inspected?	☐
Are DNS logs retained?	☐
Is data exfiltration monitored?	☐

BlackBox Pentesters Red Team Readiness Assessment

Purpose: Assess preparedness for sustained, human-led attack scenarios

Detection Maturity

This section focuses on the ability to detect realistic attacker behaviour rather than isolated alerts.

Can lateral movement be detected?	☐
Are credential abuse alerts tuned?	☐
Is behavioural monitoring deployed?	☐

Response Capability

Detection without response capability provides limited value. This section assesses whether teams can act decisively under pressure.

Is there an incident response plan?	☐
Are tabletop exercises conducted?	☐
Is containment tested?	☐

Operational Readiness

Major incidents are as much about leadership, communication, and coordination as technology. This section ensures non-technical readiness is addressed.

Is executive breach comms defined?	☐
Are legal & PR aligned?	☐
Is SOC escalation defined?	☐