Penetration Testing · Offensive Security
Prove where your defenses hold — and find the paths attackers will actually take.
You already invest in security. Cyberuptive's manual penetration testing shows you exactly where your defenses hold, where an attacker could still get in, and which fixes will move the needle first — across external and internal network, web application, cloud, and Microsoft 365 environments. We hand you assessor-ready evidence so you can walk into CMMC, PCI, HIPAA, NCUA, customer, and board conversations with proof, not opinions.
- External and internal network, web application, cloud, and Microsoft 365 penetration testing
- Phishing and social engineering scoped to your real attack surface
- Findings prioritized by exploitability, with assessor-ready reports mapped to CMMC, PCI, HIPAA, and NCUA
- Re-test of remediated findings included so fixes are verified, not assumed
What we test
Coverage that matches your real attack surface.
Most medium and large businesses do not need a $200K red team. They need a competent, scoped test of the surfaces an actual adversary would touch first: external perimeter, identity, M365, and the people who answer the phone.
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External network
Internet-facing assets: VPNs, mail, DNS, exposed services, OSINT.
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Internal network
Post-foothold lateral movement, AD abuse, kerberoasting, ACL paths.
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Web application
OWASP Top 10, business-logic flaws, auth bypass, API tests.
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Cloud
AWS, Azure, GCP misconfig, IAM blast radius, exposed buckets, key sprawl.
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Microsoft 365
Conditional access bypass, Entra ID role abuse, Exchange and SharePoint.
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Social engineering
Phishing, vishing, pretexting against named scopes you authorize.
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Wireless
WPA2/3 attacks, rogue AP detection, segmentation validation.
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Physical
Badge cloning, tailgating, lockpicking — for the rare engagement that needs it.
Methodology
PTES + NIST 800-115. Mapped to your framework.
We follow the Penetration Testing Execution Standard with NIST SP 800-115 alignment, then cross-walk findings to whatever framework your assessor cares about — CMMC 2.0, PCI DSS 4.0, HIPAA Security Rule, NCUA cyber-security guidance.
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01
Scope & ROE
Target list, blackout windows, escalation contacts, authorization letter signed.
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02
Recon & enum
OSINT, subdomain discovery, service enumeration, attack-surface mapping.
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03
Exploit & pivot
Manual exploitation, privilege escalation, lateral movement, evidence capture.
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04
Report & retest
Executive + technical report, live debrief, remediation re-test of fixed findings.
Who hires us
Defense subcontractors, regulated medium and large businesses, and the people who get audited.
We work primarily with Pacific defense supply-chain firms preparing for CMMC 2.0 Level 2 assessment, healthcare practices facing OCR scrutiny, credit unions answering NCUA exam findings, and organizations whose cyber-insurance carrier just sent a renewal questionnaire with new teeth.
If you need a clean external pen test before a C3PAO walks in, that is exactly what we do.
Common engagement profiles
- DoW subcontractor pre-CMMC: External + M365 + phishing, CUI scope review.
- Healthcare practice: External + internal + web app, HIPAA-mapped report.
- Credit union: Internal + AD + phishing, NCUA-mapped report.
- SaaS / app vendor: Web app + API + cloud, customer-trust report deliverable.
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How is your pen test different from a vulnerability scan?
A vulnerability scan tells you what is theoretically exploitable. A pen test confirms what is actually exploitable, chains issues into real attack paths, and demonstrates business impact. Scanners cannot pivot, abuse logic flaws, or social-engineer a help desk. Our testers can.
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Do you support CMMC 2.0 Level 2 testing requirements?
Yes. CMMC 2.0 Level 2 (NIST 800-171) does not mandate annual pen testing the way PCI does, but the SI and CA control families effectively require periodic security assessments. We deliver pen test artifacts that your C3PAO assessor will accept as evidence — scoped, signed, dated, and mapped to controls.
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What scopes do you cover?
External network, internal network, web application, API, cloud configuration (AWS / Azure / GCP), Microsoft 365 tenant, wireless, physical, and social engineering (phishing and vishing). Most engagements combine 2–3 scopes — a typical Pacific subcontractor engagement is external + M365 + phishing.
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How long does a typical engagement take?
Scoping: 1 week. Active testing: 1–3 weeks depending on scope. Reporting and remediation review: 1–2 weeks. Most engagements wrap in 4–6 weeks total. Re-test of fixed findings is included.
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Will testing disrupt our production systems?
No. We define a Rules of Engagement document before kickoff that specifies blackout windows, prohibited techniques (no DoS unless explicitly scoped), notification thresholds, and emergency contacts. Most testing happens against production with proper safeguards. Where appropriate we test in staging first.
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Are testers US-based and cleared?
All testers are US persons. For DoW-aligned engagements we can field cleared testers (Secret minimum) — ask during scoping. Reports are handled in CUI-aligned environments when required by DFARS 252.204-7012.
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What does a final report look like?
Executive summary (board-ready), technical findings with reproduction steps, evidence screenshots, CVSS-aligned severity, prioritized remediation roadmap, and a control-mapping appendix (CMMC, NIST, PCI, HIPAA — whichever applies). We brief your team live, not just hand off a PDF.
Aloha, let's talk
Need a pen test that an actual assessor will accept?
Tell us your scope, your framework, and your deadline. We'll come back with a fixed-scope statement of work — usually within 48 hours.