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Penetration Testing Services

Your defenses look solid on paper. We prove what breaks under pressure.

Manual, attacker-simulated exploitation — not scanner output repackaged as findings. Our senior testers chain low-severity issues into real business impact, testing the logic flaws, trust relationships, and privilege paths that automated tools structurally miss.

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Manual testing
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Critical alert
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Testing depths
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Free retest
kill-chain.sh — live engagement LIVE

01 — Recon

$ nmap -sV target.com

→ 22 services. 3 public-facing apps.

02 — Initial Access

$ exploit CVE-2024-xxxx

→ Shell obtained on web-01.

03 — Escalation

$ kerberoast --domain corp.local

→ Service account hash cracked.

04 — Lateral

$ pivot web-01 → dc-01

→ Domain Controller reached.

05 — Impact

$ dump --ntds --proof

→ Domain Admin. Full compromise.

$

Kill chain: 5/5 stages Time to Domain Admin: 4h 22min

Aligned to the standards your auditors expect

PTES NIST SP 800-115 OWASP CREST MITRE ATT&CK CVSS 4.0

// What's Included

What's Included in Our Penetration Testing Services

Our penetration testing services are structured around four phases that mirror how a real adversary operates: gather intelligence, find entry points, exploit and chain weaknesses, and document everything with evidence an engineering team can act on immediately.

Reconnaissance & OSINT

Passive and active reconnaissance to map the full external attack surface: subdomain enumeration, technology fingerprinting, exposed credentials in breach databases, public code repositories, DNS records, and open-source intelligence gathering.

Manual Exploitation

Hands-on, human-driven exploitation of identified weaknesses. Our testers craft custom payloads, bypass security controls, and validate whether each vulnerability can be leveraged to achieve unauthorized access, data exfiltration, or privilege escalation.

Chained Attack Scenarios

Individual low- and medium-severity findings are chained together into realistic multi-step attack paths. This demonstrates actual business impact: how a minor information disclosure combined with a misconfiguration can lead to full system compromise.

Detailed Evidence & Reporting

Every finding is documented with full proof-of-concept evidence: screenshots, HTTP request/response pairs, exploitation steps, CVSS 4.0 scoring, and developer-ready remediation guidance mapped to OWASP and CWE references.

// Scope

What Our Penetration Testing Services Cover

Our penetration testing services scale from a single application to your entire infrastructure. Most engagements begin with the assets closest to sensitive data or revenue-critical operations, then expand scope in subsequent cycles.

Web Applications

Authentication bypass, session hijacking, business-logic exploitation, SQL injection, XSS, SSRF, IDOR, and remote code execution testing against OWASP Top 10 and ASVS Level 2 criteria.

APIs (REST & GraphQL)

BOLA, broken function-level authorization, mass assignment, injection through query parameters, rate-limit bypass, and data exposure mapped to OWASP API Security Top 10.

Mobile Applications

Android and iOS binary analysis, insecure local storage, certificate pinning bypass, runtime manipulation, inter-process communication flaws, and API-layer testing aligned to OWASP MASVS.

Cloud Environments

AWS, Azure, and GCP penetration testing: IAM privilege escalation, storage bucket enumeration, metadata service exploitation, serverless function abuse, and cross-account trust misconfigurations.

Internal Networks & AD

Internal network penetration testing covering Active Directory enumeration, Kerberoasting, AS-REP roasting, credential relay attacks, lateral movement, and domain privilege escalation paths.

Wireless & Physical

On-site wireless penetration testing (WPA2/WPA3 assessment, rogue AP detection, evil twin attacks) and physical security testing including tailgating, badge cloning, and USB drop simulations when in scope.

// Attack Scenarios

Attack Scenarios Our Penetration Testing Services Simulate

Real attackers do not follow scanner checklists. They chain weaknesses, pivot between systems, and exploit trust relationships. Our penetration testing services replicate these multi-step attack paths to show you what an adversary can actually achieve against your environment.

External Perimeter Breach

We simulate an external attacker with no prior access attempting to breach your internet-facing perimeter. This includes port scanning, service enumeration, vulnerability exploitation on exposed services, web application attacks, and attempts to pivot from a public-facing foothold into internal systems. The objective is to determine whether an outsider can gain initial access and how far they can reach from that entry point.

How we test it

Full external attack-surface mapping using passive OSINT and active enumeration, followed by targeted exploitation of identified services, web applications, and VPN/remote-access endpoints.

Privilege Escalation Chains

Once initial access is obtained, we attempt to escalate privileges from a low-level user to administrator or root. This involves exploiting misconfigurations in sudo rules, SUID binaries, scheduled tasks, service accounts with excessive permissions, and kernel or OS-level vulnerabilities. On Windows systems, we test for unquoted service paths, DLL hijacking, and token impersonation opportunities.

How we test it

Systematic enumeration of local privilege escalation vectors on each compromised host, combined with automated tooling (LinPEAS, WinPEAS, BloodHound) and manual verification of each escalation path.

Active Directory Compromise

Active Directory is the backbone of most enterprise networks, and its compromise typically means full domain control. We test for Kerberoasting, AS-REP roasting, unconstrained delegation abuse, credential relay attacks (NTLM relay, PetitPotam), GPO abuse, and DCSync. We map every privilege escalation path from a standard domain user to Domain Admin using BloodHound analysis.

How we test it

BloodHound enumeration of AD trust relationships, manual Kerberos ticket analysis, credential relay attempts, and exploitation of identified escalation paths from standard user to Domain Admin.

Cloud Account Takeover

In cloud-native environments, the attack surface shifts to IAM policies, instance metadata services, serverless function configurations, and cross-account trust relationships. We test for SSRF-to-IMDS credential extraction, overly permissive IAM roles, publicly exposed storage buckets with sensitive data, and misconfigured cross-account trust policies that allow unauthorized access from external accounts.

How we test it

Cloud-specific enumeration using Pacu (AWS), ScoutSuite, and manual IAM policy analysis. SSRF testing against metadata endpoints, storage enumeration, and privilege escalation through misconfigured roles and policies.

API Chain Exploitation

APIs often expose more functionality than intended. We chain together IDOR vulnerabilities, broken function-level authorization, mass assignment flaws, and injection points across multiple API endpoints to demonstrate realistic attack paths. A single low-severity information disclosure on one endpoint can be combined with a mass-assignment flaw on another to achieve full account takeover or data exfiltration.

How we test it

Full API endpoint enumeration, multi-role authorization matrix testing, parameter fuzzing, and systematic chaining of individual findings into multi-step exploitation paths.

Social Engineering & Phishing

Technical controls mean little if an employee can be convinced to hand over credentials or execute a malicious payload. We design and execute targeted phishing campaigns using realistic pretexts based on OSINT gathered during reconnaissance. This includes credential-harvesting pages, payload delivery via email attachments, and vishing (voice phishing) calls where scope permits.

How we test it

Custom phishing infrastructure with tracking, realistic pretext development based on OSINT, and detailed reporting on click rates, credential submissions, and payload execution rates.

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Manual testing coverage per engagement

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Avg. exploitable findings per engagement

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Critical-finding escalation time

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Findings retested at no cost

// Methodology

How Our Penetration Testing Engagement Works

Five phases. PTES and NIST SP 800-115 aligned. From scoping to signed closure report — every step documented, every finding retested.

pentest-engagement.sh — CipherTrivia

#!/bin/bash — pentest-engagement

$ scope --rules-of-engagement --test-window

→ Targets defined. Black/grey/white box agreed.

✓ Engagement scoped — Week 0

$ recon --osint --enum --fingerprint

→ External surface mapped. 47 services. 3 entry points.

✓ Attack surface inventory — Week 1

$ exploit --chain --pivot --escalate

✗ Initial access → lateral movement → Domain Admin.

✓ Exploitation complete — Week 1-2

$ post-exploit --persist --exfil --impact

✗ Data exfil validated. Persistence established.

✓ Impact documented — Week 2

$ report --cvss4 --attack-paths --retest

→ 12 findings. Attack chain diagrams. Walkthrough done.

✓ Closure report after retest — Week 3

$

01

Planning & Rules of Engagement

Define scope, objectives, testing windows, communication protocols, and rules of engagement. Identify in-scope targets, out-of-scope systems, constraints (no DoS, no production data modification). Obtain formal authorization. Agree on black-box, grey-box, or white-box approach and establish emergency contact procedures.

Scoping RoE Sign-off Authorization
Week 0 · Output: Signed engagement letter
02

Reconnaissance & Enumeration

Passive and active intelligence gathering: OSINT collection, subdomain enumeration, technology fingerprinting, port and service scanning, credential breach-database searches. Map the full external and internal attack surface before any exploitation begins.

OSINT Service Enum Fingerprinting
Week 1 · Output: Attack surface inventory
03

Exploitation & Pivoting

Manual exploitation using custom payloads and established tooling. Bypass security controls, escalate privileges, and pivot to additional systems. Chain low-severity issues into high-impact attack paths that demonstrate real business risk — from initial foothold to lateral movement to domain-level access.

Custom Exploits Pivoting Priv Escalation
Week 1-2 · Output: Exploitation evidence
04

Post-Exploitation & Impact Validation

Assess what an attacker could achieve from each compromised position: credential harvesting, data exfiltration proof, persistence mechanisms, and potential for domain-wide compromise. Document the full attack chain from initial entry to maximum achievable impact.

Data Exfil PoC Persistence Impact Analysis
Week 2 · Output: Full attack chain documentation
05

Reporting, Walkthrough & Retest

Prioritized report with CVSS 4.0 scores, full proof-of-concept evidence, attack-chain diagrams, and developer-ready remediation guidance. Live walkthrough with your engineering team. Free retest of every finding once fixed. Signed closure report for auditors and customers.

CVSS 4.0 Report Live Walkthrough Free Retest
Week 3 · Output: Report + closure certificate

// Deliverables

What You Receive From Our Penetration Testing Services

Every penetration testing engagement produces a complete set of deliverables designed for three audiences: engineers who need to fix the issues, leadership who needs to understand the risk, and auditors who need formal evidence of due diligence.

01

Executive Summary

A concise overview of overall risk posture, key findings, and business impact written for non-technical stakeholders and board-level reporting.

02

Technical Findings Report

Every exploited vulnerability documented with CVSS 4.0 scoring, full proof-of-concept evidence, HTTP request/response captures, screenshots, and step-by-step reproduction instructions.

03

Attack-Chain Diagrams

Visual maps of every multi-step attack path exploited during the engagement, showing how individual weaknesses were chained to achieve broader compromise.

04

Remediation Guidance

Developer-ready fix guidance for every finding, with specific code-level or configuration-level recommendations mapped to OWASP, CWE, and MITRE ATT&CK references.

05

Free Retest & Closure Report

Once findings are remediated, we retest every issue at no extra cost and deliver a signed closure report confirming fix status, ready for auditors, regulators, and enterprise customers.

Five deliverables. One engagement. Everything your team and your auditors need.

Request a sample report

// Why CipherTrivia

Why Choose CipherTrivia for Penetration Testing Services

There are meaningful differences between a penetration test that produces actionable results and one that repackages scanner output. Here is what sets our penetration testing services apart.

Senior Testers, Not Juniors With Scanners

Every engagement is led by experienced penetration testers who manually validate every finding. No scanner-only reports. No unvalidated output passed off as testing.

Chained Exploits, Not Isolated Findings

We chain individual vulnerabilities into realistic multi-step attack paths to demonstrate actual business impact, not just theoretical risk ratings on isolated issues.

Zero False-Positive Noise

If a finding is in your report, it has been exploited and confirmed. Your engineering team spends time remediating real vulnerabilities, not triaging scanner noise.

Compliance-Ready Reports

Reports map directly to ISO 27001, SOC 2 Type II, PCI DSS, HIPAA, and GDPR evidence requirements. No rework needed before your next audit cycle.

// Proof of Work

A Penetration Testing Case Study

Penetration Test · Banking & Fintech

Closing Critical Gaps in a Banking API Gateway

A regional bank required a full penetration test of its customer-facing API gateway ahead of a production launch. Our testers identified 9 exploitable issues, including a critical broken access control flaw that allowed cross-account data access. All findings were remediated and retested within a 3-week deadline.

Read case study

// FAQ

Frequently Asked Questions About Penetration Testing Services

What is the difference between penetration testing and vulnerability scanning?

Vulnerability scanning is automated: a tool checks your systems against a database of known weaknesses and produces a list. Penetration testing goes further. A human tester takes those findings, chains them together, and attempts real exploitation to determine what is actually exploitable in your specific environment. Scanners report possibilities; penetration testers confirm realities. A vulnerability scan might flag an open port, but a penetration test will determine whether that port can be leveraged to gain unauthorized access to internal systems, escalate privileges, or exfiltrate data.

How often should an organization conduct penetration testing?

At minimum, once per year and after any significant infrastructure or application change. Compliance frameworks such as PCI DSS require annual penetration tests explicitly. Organizations with continuous deployment pipelines, frequent feature releases, or high-risk data (financial, healthcare, PII) benefit from quarterly or semi-annual testing cycles. We also recommend an ad-hoc test before any major product launch, merger-related system integration, or cloud migration.

Will penetration testing cause downtime or disrupt production systems?

Our rules of engagement are defined before any testing begins. We agree on testing windows, rate limits, and explicitly excluded actions such as denial-of-service or destructive write operations. Where possible, testing runs against staging environments. When production testing is required, we coordinate timing with your operations team, use throttled techniques, and maintain a direct communication channel throughout the engagement so any concern can be addressed immediately.

What standards and frameworks do your penetration tests follow?

Our penetration testing methodology is aligned to PTES (Penetration Testing Execution Standard) and NIST SP 800-115 (Technical Guide to Information Security Testing and Assessment). Findings are scored using CVSS 4.0 and mapped to OWASP Top 10, OWASP API Security Top 10, CWE, and MITRE ATT&CK where applicable. Reports are structured to satisfy evidence requirements for ISO 27001, SOC 2 Type II, PCI DSS, HIPAA, and GDPR audits.

Do you provide a retest after vulnerabilities are fixed?

Yes. Every penetration testing engagement includes one full retest cycle at no additional cost. Once your engineering team has remediated the findings, we re-verify each issue individually and issue a signed closure report confirming the fix status. This closure report is the document most auditors and enterprise customers request as evidence that identified risks have been addressed.

Get Started With Our Penetration Testing Services

Tell us about your application, API, cloud, or network environment and we will scope a penetration testing engagement that fits your timeline, compliance requirements, and budget.