Without proper planning, you risk wasting time, money, and the chance to identify and fix real vulnerabilities. This guide shows IT managers and CTOs how to prepare effectively.
It covers technical steps, internal coordination, and strategic considerations—so your company gets the maximum benefit from the engagement.
If you want to reduce your attack surface, meet compliance goals, or protect sensitive data, read on.
Know Why You Are Doing the Pen Test
Define your goals first. Why are you doing this test?
Is it to:
- Comply with regulations like PCI-DSS, HIPAA, or ISO 27001?
- Fulfill a client or third-party contract requirement?
- Review your environment after a major upgrade or migration?
- Identify weak points by simulating a real-world attack?
- Prepare for an audit or certification?
The scope, methods, and tools of the test all depend on your goals.
At Wyrdex, we start here ensuring every test aligns with your business needs, not just a checklist of technical requirements.
Pick the Right Scope
Next, determine what the test will cover.
What assets or systems are in scope? What’s excluded?
Common areas include:
- Web applications
- Internal networks
- External IP addresses
- Cloud infrastructure
- Servers and endpoints
- Wireless networks
- Mobile applications
- Internet of Things (IoT) devices
- Physical security (in Red Team exercises)
Defining scope early is critical.
- Too broad: focus is lost and noise increases.
- Too narrow: key exposures may be missed.
Wyrdex helps clients define a smart, business-driven scope based on architecture and logic.
Choose the Test Type: Black, White, or Grey Box
Three common types of penetration tests:
- Black Box
Testers have no prior knowledge, simulating an external attacker. - White Box
Testers have full knowledge (documentation, source code, credentials). Best for inside-out testing. - Grey Box
A middle ground limited knowledge, like a compromised account or insider threat.
Each has pros and cons. Choose based on your risk tolerance and threat model.
Wyrdex often recommends Grey Box testing it provides realistic results without wasting time on pure reconnaissance.
Inform Internal Stakeholders
Surprise is fine for Red Team simulations but not for standard penetration testing.
Notify the following before testing begins:
- IT staff (to distinguish test activity from real attacks)
- Security teams (to monitor detection capabilities)
- Helpdesk (to avoid unnecessary tickets or escalations)
- Legal and compliance teams (for reporting and documentation needs)
- Cloud or infrastructure providers (if hosted environments are involved)
Also, check that monitoring tools are working correctly.
Make sure alerts won’t automatically trigger containment unless intended.
Clear communication prevents confusion and ensures useful results.
Identify Sensitive Systems and Business Limitations
Not all systems can be tested the same way. Flag systems that:
- Process financial transactions
- Handle patient or healthcare data
- Must meet strict SLAs or uptime guarantees
- Cannot withstand stress testing during business hours
For these, schedule low-risk testing windows or use staging environments.
At Wyrdex, we always confirm these limitations in advance to ensure business continuity.
Fix Known Issues First
Don’t waste time testing weaknesses you already know about.
Before testing:
- Apply security patches
- Update outdated libraries and frameworks
- Disable unused ports and services
- Remove or secure default credentials
- Review SSL/TLS configurations
- Check endpoint and firewall rules
This isn’t about hiding issues it ensures the test focuses on unknown risks.
Wyrdex advises clients to resolve “low-hanging fruit” first, so we can uncover deeper vulnerabilities.
Provide Temporary Test Accounts and Credentials
For White or Grey Box tests, prepare:
- Temporary user accounts with defined roles
- API keys or tokens with limited scope
- VPN or portal access for internal testing
Keep these separate and revoke them immediately after the test.
For privilege escalation, testers attempt to move from regular user to domain admin don’t grant admin access upfront unless it’s a code review.
Back Up Critical Systems
Even with careful planning, outages may occur.
Ensure full, recent, and restorable backups for:
- Production servers
- Databases
- Web applications
- Cloud resources
This is your final safeguard. With reliable backups, recovery is quick if disruptions happen.
Plan for After the Test
The test is only the beginning.
Decide in advance:
- Who will review the final report?
- Who will own remediation tasks?
- Timelines for fixing vulnerabilities
- Whether retesting will be done
Act quickly once findings are reported. Assign each issue an owner and a deadline.
At Wyrdex, we provide:
- Executive summaries (non-technical)
- Detailed technical vulnerability reports
- Risk ratings (CVSS-based)
- Screenshots and proof-of-concepts
- Remediation support
- Optional retesting
You’re not just buying a report—you’re investing in a stronger security posture.
Understand Vulnerability Scanning vs. Penetration Testing
These are not the same.
- Vulnerability Scanning: Automated, identifies known CVEs, produces reports.
- Penetration Testing: Human-led, uses attacker logic, chains misconfigurations, and bypasses controls.
If your last “pen test” was just a Nessus scan with a PDF, you didn’t get a real test.
Wyrdex combines automation and manual expertise to reveal risks that truly matter.
Focus on Business Impact
The best pen tests go beyond technical flaws.
Not just: “Page X has SQL injection.”
But:
- “This flaw exposes your customer database.”
- “This chain allows pivoting from a web form to your payroll server.”
At Wyrdex, every finding highlights business impact data, reputation, compliance, and availability.
This helps you prioritize remediation and communicate effectively to executives.
Use the Test to Drive Security Culture
A penetration test shouldn’t be a one-off event.
Use it to:
- Increase team awareness
- Train junior IT or development staff
- Justify cybersecurity investments
- Update your risk register
- Test incident response capabilities
- Improve policies, architectures, and controls
A good pen test sparks lasting improvements. Wyrdex helps clients use findings to create real change.
Why Choose Wyrdex for Penetration Testing
Wyrdex is more than a cybersecurity vendor—we are a full-service Managed Security Service Provider (MSSP) with both offensive and defensive expertise.
Our services include:
- Internal and external network penetration testing
- Web and mobile application security testing
- API and cloud security assessments
- Red Team and social engineering exercises
- Compliance-aligned testing (PCI-DSS, GDPR, HIPAA, ISO 27001)
- Actionable reporting with remediation guidance
- Retesting and validation included
We think like attackers. We go beyond scanning. We collaborate.
With Wyrdex, penetration testing prepares you for compliance, reassures investors, and strengthens your defenses.
Final Thoughts
Penetration testing isn’t about proving perfection.
It’s about finding weaknesses before attackers do and fixing them fast.
With preparation, alignment, and the right partner, a pen test strengthens your entire organization’s security.
Be proactive. Book your penetration test with Wyrdex today before someone else finds your blind spots.