Penetration Testing: What to Expect and How to Prepare
A penetration test (pen test) is a simulated cyberattack conducted by authorized security professionals to identify vulnerabilities in your network, applications, and processes before real attackers exploit them.
Why Pen Testing Matters:
Vulnerability scanners find known issues. Pen testers think like attackers — they chain together multiple weaknesses, exploit misconfigurations, and test human defenses to achieve objectives that scanners cannot simulate.
Types of Penetration Tests:
External Network Pen Test
Tests your internet-facing infrastructure: firewalls, VPNs, web servers, email gateways, DNS, and cloud services. - Attackers can see your public IP ranges and domains - Tests for: open ports, unpatched services, misconfigurations, credential stuffing - Duration: 3-5 days - Cost: $3,000-$10,000
Internal Network Pen Test
Tests what an attacker can do once inside your network (simulating a compromised employee, visitor, or device). - Tester plugs into your network or uses VPN access - Tests for: lateral movement, privilege escalation, sensitive data access, Active Directory weaknesses - Duration: 3-5 days - Cost: $5,000-$15,000
Web Application Pen Test
Tests specific web applications for OWASP Top 10 vulnerabilities. - Tests for: SQL injection, XSS, authentication bypass, authorization flaws, API vulnerabilities - Duration: 3-7 days per application - Cost: $5,000-$20,000
Wireless Pen Test
Tests Wi-Fi security, rogue APs, and wireless client attacks. - Tests for: weak encryption, rogue access points, evil twin attacks, client isolation - Duration: 1-3 days on-site - Cost: $2,000-$8,000
How to Prepare for a Pen Test:
1. **Define scope:** Which systems, networks, and applications are in scope? Exclude anything you do not want tested (production databases, life-safety systems).
2. **Get authorization:** Written authorization from organizational leadership. Include legal protections for the testing team.
3. **Notify your team:** Tell your IT team and MSP that a test is happening (unless testing incident detection). Provide emergency contacts.
4. **Share documentation:** Network diagrams, IP ranges, application URLs, user accounts for authenticated testing.
5. **Prepare monitoring:** Have your SOC/MSP actively monitor during the test. This is also a test of your detection capabilities.
6. **Schedule wisely:** Avoid peak business periods. External tests can run anytime; internal tests usually require on-site presence.
What the Report Should Include:
- Executive summary (non-technical, for leadership)
- Methodology (what was tested and how)
- Findings with severity ratings (Critical, High, Medium, Low, Informational)
- Evidence (screenshots, packet captures, proof of exploitation)
- Remediation recommendations prioritized by risk
- Retesting provisions (verify fixes were effective)
Pen Testing Frequency:
- Annually at minimum for all businesses - After significant infrastructure changes (cloud migration, new application, network redesign) - Quarterly for organizations in regulated industries (PCI-DSS requires annual pen test) - After a breach or security incident (verify remediation effectiveness)
Choosing a Pen Testing Firm:
- Look for OSCP, OSCE, GPEN, or CREST-certified testers - Ask for sample reports to evaluate quality and depth - Ensure they carry professional liability insurance - Verify they use a defined methodology (OWASP, PTES, NIST) - Check references from businesses in your industry
Summit DNC partners with certified penetration testing firms and coordinates the entire process — scoping, scheduling, remediation, and retesting. We also implement the fixes identified during testing as part of our managed IT services. Contact us to schedule a pen test.
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Social Engineering Pen Test
Tests human defenses via phishing campaigns, phone pretexting, and physical security assessments. - Tests for: phishing click rates, credential harvesting, tailgating, badge cloning - Duration: 2-4 weeks (includes campaign design and execution) - Cost: $3,000-$10,000