What to Expect During a Penetration Test
#education
A penetration test (or pentest) isn't just "hacking" your systems—it's a controlled simulation of a real-world cyberattack, done with your permission, to uncover vulnerabilities before criminals can exploit them.
If you've never undergone a pentest before, it can feel intimidating. But understanding the process ahead of time can make it a valuable, even exciting, part of strengthening your security.
In this post, we'll walk through what to expect during a penetration test—from kickoff to final report—so you and your team are fully prepared.
🧠 Why Do a Penetration Test?
Think of a pentest as a stress test for your security posture. Just like a fire drill helps you prepare for a real emergency, a pentest uncovers:
- Gaps in network defenses
- Misconfigured systems
- Weak passwords or access controls
- Vulnerable web applications or exposed data
According to IBM's Cost of a Data Breach Report 2024, the average cost of a breach is $4.45 million. Pentesting is one of the most cost-effective ways to identify and patch risks before they become headlines.
🔍 The Penetration Testing Lifecycle
Here's a breakdown of the typical stages in a professional pentest:
📅 1. Scoping & Planning
Before any testing begins, your security partner will meet with you to:
- Define the scope (what's in or out of bounds)
- Determine test type (external, internal, web app, cloud, etc.)
- Set rules of engagement (when and how testing occurs)
- Identify goals (e.g., test for lateral movement, data exfiltration)
What you'll discuss:
- Which systems are in scope
- Testing windows (business hours vs. after-hours)
- Communication protocols during testing
- Emergency contact procedures
- Any systems or data that are off-limits
⚠️ Nothing is tested without approval. This phase ensures safety and clarity for both sides.
🔦 2. Reconnaissance
Also called information gathering, this is where testers identify:
- Public-facing systems and services
- Domain and DNS records
- Employee emails and public data leaks
- Tech stack (web servers, frameworks, etc.)
What happens:
- Passive information gathering (no direct interaction with your systems)
- OSINT (Open Source Intelligence) collection
- Social media and public data analysis
- DNS enumeration and subdomain discovery
Tools commonly used: Amass, Nmap, Shodan, theHarvester, crt.sh
What you'll see: Minimal impact—this phase is mostly passive and won't affect your systems.
🧪 3. Scanning & Enumeration
Next, testers perform in-depth mapping of your systems:
- What ports and services are open?
- Are outdated or vulnerable services exposed?
- Are there misconfigurations (e.g., open S3 buckets, default creds)?
What happens:
- Port scanning to identify open services
- Service version detection
- Vulnerability scanning
- Configuration analysis
The goal is to build a picture of your environment from an attacker's perspective.
What you'll see: Increased network traffic and log entries. Your monitoring systems may alert—this is expected and normal.
🧨 4. Exploitation
This is the meat of the test—where the tester attempts to:
- Bypass authentication
- Escalate privileges
- Exploit known vulnerabilities (e.g., Log4Shell, SQL injection)
- Access sensitive data
What happens:
- Attempts to exploit identified vulnerabilities
- Authentication bypass attempts
- Privilege escalation testing
- Data access attempts
🔐 Note: A good tester avoids disrupting services and gets permission before attempting risky exploits like DoS attacks.
What you'll see:
- Failed login attempts in logs
- Unusual access patterns
- Security alerts (this is expected)
- No service disruption if testing is done correctly
🕵️ 5. Post-Exploitation & Lateral Movement
If access is gained, the tester will simulate:
- Data exfiltration
- Persistence (e.g., setting backdoors)
- Lateral movement (jumping from one system to another)
What happens:
- Testing how deep an attacker could go after gaining initial access
- Simulating data theft scenarios
- Testing network segmentation effectiveness
- Identifying privilege escalation paths
This phase tests how deep an attacker could go after gaining a foothold.
What you'll see: If vulnerabilities are found, you may see:
- Unusual file access
- Network connections between systems
- Modified configurations (temporary, for testing)
📝 6. Reporting
Once testing is complete, you'll receive a detailed report including:
- Executive summary (non-technical, for leadership)
- Technical findings with severity levels (Critical, High, Medium, Low)
- Proof-of-concept for each exploit (screenshots, code, evidence)
- Recommendations and remediation guidance
- Risk assessment and business impact analysis
Report structure typically includes:
- Overview of testing methodology
- Summary of findings by severity
- Detailed technical write-ups
- Remediation steps with priorities
- Compliance mapping (if applicable)
Some firms (like M Square LLC) also offer a debrief session to walk you through the report and answer questions.
🔁 7. Retesting (Optional, but Recommended)
After you fix the issues, your security team may perform a retest to confirm vulnerabilities are resolved and no new ones were introduced during the fix process.
What happens:
- Targeted testing of previously identified vulnerabilities
- Verification that fixes are effective
- Check for regression (new issues introduced by fixes)
Timeline: Usually 2-4 weeks after remediation, depending on scope.
🧩 Types of Penetration Tests
| Test Type | Description | What Gets Tested |
|---|---|---|
| External | Focuses on internet-facing systems | Web apps, VPNs, email servers, public APIs |
| Internal | Simulates an attacker who's breached your perimeter | Network segmentation, Active Directory, internal systems |
| Web App/API | Looks for OWASP Top 10 risks and business logic flaws | Authentication, authorization, injection flaws, XSS |
| Wireless | Assesses Wi-Fi encryption, access, rogue devices | WPA/WPA2 security, guest network isolation, rogue APs |
| Social Engineering | Tests your employees via phishing or impersonation | Phishing campaigns, pretexting calls, physical access |
| Physical | Tests building access and physical security controls | Badge access, server room security, tailgating |
📌 What You Should Prepare
To ensure a smooth pentest:
Before Testing Begins
- Designate a point of contact — Someone who can answer questions and make decisions during testing
- Whitelist tester IPs if needed — Some organizations require IP whitelisting for testing
- Backup systems before the test — Always have a backup, just in case
- Inform your IT team — Especially important during internal testing
- Review scope document — Make sure everyone understands what's being tested
During Testing
- Be available — Respond to questions or concerns promptly
- Monitor your systems — Watch for alerts, but don't panic—testing will generate alerts
- Document any issues — Note any unexpected behavior or concerns
- Be ready to respond — If critical findings emerge, be prepared to act quickly
After Testing
- Review the report — Take time to understand the findings
- Prioritize remediation — Focus on critical and high-severity issues first
- Ask questions — Don't hesitate to request clarification
- Plan retesting — Schedule retesting after fixes are implemented
🤝 What Makes a Good Penetration Test Partner?
Look for:
- Clear communication and transparency throughout the process
- Experience with your industry or compliance needs (HIPAA, PCI-DSS, SOC 2, etc.)
- Certifications like OSCP, CEH, CISSP, GPEN
- A focus on education—not just breaking things
- Detailed reporting with actionable recommendations
- Post-test support and remediation guidance
💬 At M Square LLC, we go beyond the test. We educate your team, provide remediation support, and treat each engagement as a partnership—not a one-off job.
⏱️ Typical Timeline
| Phase | Duration | What's Happening |
|---|---|---|
| Scoping | 1-2 weeks | Planning, documentation, approvals |
| Reconnaissance | 1-3 days | Passive information gathering |
| Scanning & Enumeration | 2-5 days | Active scanning and mapping |
| Exploitation | 3-7 days | Attempting to exploit vulnerabilities |
| Post-Exploitation | 1-3 days | Lateral movement and data access testing |
| Reporting | 1-2 weeks | Report writing and review |
| Debrief | 1-2 hours | Walkthrough and Q&A session |
| Retesting | 1-3 days | Verification of fixes |
Total timeline: Typically 3-6 weeks from kickoff to final report, depending on scope and complexity.
🚨 Common Concerns (And Why They're Usually Unfounded)
"Will testing break our systems?"
Answer: No. Professional testers avoid destructive actions and get approval before risky exploits. Your systems should remain operational throughout testing.
"Will testing expose sensitive data?"
Answer: Testers follow strict confidentiality agreements. Any data accessed is documented in the report but not shared outside your organization.
"What if we find nothing?"
Answer: That's actually good news! It means your defenses are working. The report will still document what was tested and provide recommendations for maintaining security.
"How do we know the tester is qualified?"
Answer: Look for certifications (OSCP, CEH, CISSP), experience, and references. Ask about their methodology and reporting process.
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🧠 Final Thoughts
A penetration test shouldn't be something you fear—it should be something you look forward to.
It's a chance to challenge your defenses in a safe environment, learn where the cracks are, and fix them before a real attacker finds them.
Whether you're prepping for compliance or just want to sleep better at night, a penetration test is one of the smartest investments you can make in your cybersecurity strategy.
✅ Want to See What a Pentest Looks Like?
Book a free consultation with M Square LLC and we'll walk you through the exact steps, scope, and timeline tailored to your business.
Questions about penetration testing? Reach out directly:
- Email: m1k3@msquarellc.net
- Phone: (559) 670-3159
- Schedule: Book a free consultation
📅 On-site and virtual testing available
📚 Further Reading and References
- NIST Penetration Testing Guide (SP 800-115)
- OWASP Testing Guide
- IBM Cost of a Data Breach Report 2024
- CISA Vulnerability Scanning Services
M Square LLC
Cybersecurity | Penetration Testing | No-Nonsense Advice