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Penetration Testing & Security Assessments

// We break it before attackers do.

Real Adversary Simulation. SMB-Accessible Pricing.

Most penetration testing firms price small and medium-sized businesses out of the market entirely — treating a thorough security assessment as a luxury only enterprise clients can afford. We’ve built our practice to bridge that gap. The threat doesn’t scale with your budget; the assessment should. Beyond business sense, compliance is driving demand: CMMC Level 2 requires third-party assessments for any contractor handling Controlled Unclassified Information (CUI). Healthcare organizations face HIPAA breach liability. Payment processors face PCI-DSS scope creep. And across every vertical, attackers are automating their reconnaissance while defenders are still catching up. A professional penetration test tells you — with evidence, not theory — exactly where you stand before someone with worse intentions finds out first.

Penetration Testing Services

Network Penetration Test

External and internal network assessments targeting firewalls, routers, switches, exposed services, and lateral movement paths. We enumerate what’s reachable and prove what’s exploitable.

Web Application Testing

Manual and tool-assisted testing of web apps against OWASP Top 10 and beyond: injection flaws, broken authentication, SSRF, IDOR, business logic abuse, and insecure direct object references.

Social Engineering & Phishing

Realistic pretexting campaigns, spear-phishing simulations, and vishing tests against your staff. Identifies human-layer exposure before a real threat actor exploits it.

External Attack Surface Review

Full enumeration of your internet-facing footprint — domains, subdomains, exposed ports, leaked credentials, and certificate transparency findings — from an attacker’s perspective.

Internal Network Assessment

Simulates a compromised endpoint or insider threat. We map Active Directory, hunt for misconfigurations, test privilege escalation paths, and identify lateral movement opportunities.

Cloud Configuration Review

AWS, Azure, and GCP configuration assessments targeting IAM misconfigurations, overly permissive storage buckets, exposed APIs, and insecure secrets management.

Compliance-Driven Assessment

Penetration testing scoped to CMMC Level 2, HIPAA Security Rule, and PCI-DSS requirements. Delivers the documented evidence your assessor or auditor needs.

Remediation & Retesting

After you fix identified vulnerabilities, we retest to confirm closure. Not a new engagement — included as part of the original assessment so you can show verified remediation.

Wireless Security Assessment

Wi-Fi security testing targeting WPA2/WPA3 configurations, rogue access point detection, Evil Twin scenarios, and wireless client attacks. We assess both the RF environment and the network architecture it connects to.

pentester@ottomateit:~$ nmap -sV -p- --open 203.0.113.42
Starting Nmap 7.95 ( https://nmap.org )
Scanning 203.0.113.42 [65535 ports]
PORT      STATE SERVICE      VERSION
22/tcp    open   ssh          OpenSSH 7.4 (protocol 2.0)
80/tcp    open   http         Apache httpd 2.4.6
443/tcp   open   ssl/http     Apache httpd 2.4.6
8080/tcp  open   http-proxy   [!] version disclosure detected
8443/tcp  open   ssl/http     [!] self-signed cert, expired 2022
Nmap done: 1 IP address (1 host up) scanned in 214.33s
// findings queued for manual exploitation phase — proceeding

Our Methodology

We follow a structured, rules-of-engagement-driven process. Every engagement begins with a signed scope document and ends with verified remediation — nothing happens outside agreed boundaries.

  1. Scoping. Define the target environment, engagement rules, out-of-scope systems, testing windows, and emergency contacts. You know exactly what we will and won’t touch before a single packet is sent.
  2. Reconnaissance. Passive and active information gathering — OSINT, DNS enumeration, certificate transparency, leaked credential databases, and external asset discovery. We think like the attacker before we act like one.
  3. Scanning & Enumeration. Service discovery, version fingerprinting, vulnerability scanning, and directory brute-forcing. We build a complete picture of the attack surface.
  4. Exploitation. Manual exploitation of confirmed vulnerabilities using the same tools and techniques real adversaries use — with care and precision, not automation alone. Every exploit is documented with timestamps and evidence.
  5. Post-Exploitation. Where scope allows: privilege escalation, credential harvesting, lateral movement, and data access demonstration. We answer the real question: how far could an attacker actually get?
  6. Reporting. Findings are documented in both an executive summary and a technical deep-dive. Every vulnerability includes a CVSS score, proof-of-concept evidence, business impact statement, and a concrete remediation recommendation.
  7. Remediation Support. We answer questions, clarify findings, and help your team prioritize fixes. The report doesn’t go in a drawer — we walk you through it.
  8. Retest. After remediation work is complete, we verify that identified vulnerabilities are closed and no regression has introduced new exposure. Documented closure included in the deliverable package.

Who Needs a Penetration Test

CMMC Contractors

DoD suppliers handling CUI must demonstrate third-party security assessment under CMMC Level 2. A penetration test is evidence — not optional.

Healthcare Organizations

HIPAA doesn’t mandate pen testing by name, but the Security Rule requires a thorough risk analysis. Documented exploitation findings satisfy that requirement far better than a checklist.

Financial Services

Banks, RIAs, credit unions, and payment processors face PCI-DSS scope requirements and GLBA safeguards rules that increasingly point to external testing as table stakes.

Any Business Storing PII or Cardholder Data

If you collect names, SSNs, payment card numbers, or health records, your liability in a breach is proportional to how well you tested your own defenses beforehand.

Law Firms

Client confidentiality is a professional obligation. A compromised matter file or leaked M&A deal is a reputational catastrophe. Pen tests are increasingly required by large corporate clients as a vendor condition.

Government Contractors

Beyond CMMC, many federal contract vehicles, GSA schedules, and agency-specific security requirements include penetration testing as a contractual obligation or evaluation criterion.

What You Get

Every engagement delivers a complete, actionable package — not a wall of scanner output with a cover page stapled to it.

Authoritative Resources

These are the standards and frameworks we work from. Reviewing them yourself will help you ask better questions of any pen testing provider:

Schedule a Free Scoping Call

We’ll define the target, answer your questions, and give you a clear picture of what a professional assessment covers — before you commit to anything.

Schedule a Free Scoping Call