How To Perform An Internal Penetration Test In The Covid-19 Era

Understanding Internal Penetration Testing In The COVID-19 Era

Internal penetration testing simulates attacks from within your network perimeter, emulating a compromised endpoint or malicious insider. 

Unlike external tests, focused on firewalls and public-facing assets, an internal pentest drills into VPN gateways, file shares, cloud workloads, and employee workstations.

Remote work has introduced shadow IT (unauthorized apps and devices), home-router misconfigurations, and VPN overloads as prime attack surfaces. 

A thorough internal pentest today must account for both corporate hardware and personal endpoints used for business tasks.

What is internal penetration testing, and why does it matter?

Internal pentesting reveals hidden exposures behind your firewall—critical when remote endpoints and cloud services expand the attack surface.

Why Remote Internal Pentesting Is Essential for Distributed Workforces

Shifting to remote operations has tangible security impacts.  

In 2024, IBM’s Cost of a Data Breach Report found the global average breach cost reached $4.88 million, a 10 percent jump year-over-year. 

When remote work was identified as a factor, organizations incurred an additional $173,074 on average compared to breaches without a remote-work component. 

Moreover, 52 percent of organizations reported experiencing at least one cybersecurity incident attributable to remote work in 2023, underscoring how distributed endpoints amplify risk. 

Competitor guides often overlook secure VPN configuration, cloud-tenant isolation, and insider-movement simulation gaps that this guide will fill.

Step 1: Preparing Your Work-From-Home Environment for an Internal Pentest

1. Device Inventory: Catalog all endpoints—laptops, desktops, mobile devices—and note OS versions and patch status.
   
   
2. Network Mapping: Identify home-router models, IoT devices and personal NAS units. Check for default credentials or outdated firmware.
   
   
3. Secure Baselines: Apply hardening guidelines: disable unused services, enforce disk encryption and enable host-based firewalls.
   
   
4. Log Collection: Ensure remote-access logs (VPN, RDP) are forwarded to a central SIEM or log-aggregation service.
   
   
5. Work from Home Vulnerability Scan: Run automated scans (e.g., Nessus, OpenVAS) against endpoints and home networks to flag missing updates, open ports or weak ciphers.

These preparatory steps create a reliable snapshot of your distributed inventory—vital for a thorough internal pentest.

Step 2: Scoping & Planning Your COVID-19 Era Internal Pentest

• Define Objectives: Align testing goals with risk appetite—data exfiltration, privilege escalation or compliance validation.
  
  
• Asset In-Scope: Include VPN concentrators, cloud instances (AWS, Azure), collaboration suites (Microsoft 365, Google Workspace) and remote-desktop servers.
  
  
• Checklist Creation: Develop an internal penetration test checklist for work-from-home environments that covers endpoint hardening, VPN split-tunneling, cloud-storage permissions, and employee-owned devices.
  
  
• Compliance Alignment: Reference regulatory mandates (PCI DSS 11.3.1, ISO 27001 A.12.6.1) to ensure your scope meets audit requirements.
  
  
• Timeline & Rules of Engagement: Establish testing windows to minimize business disruption, and document acceptable tools, techniques, and escalation paths.

A clear plan and checklist guarantee full coverage of pandemic-era risks.

Step 3: Conducting Network Penetration Tests Remotely

1. Automated Scanning: Launch credentialed and non-credentialed scans via VPN or remote agents. Tools like Nmap, Nessus, and Qualys can enumerate open ports, services, and misconfigurations.
   
   
2. Manual Verification: Validate automated findings through manual techniques—banner grabbing, custom scripts, or targeted exploits.
   
   
3. Remote Exploitation: Leverage VPN-authenticated sessions to pivot into internal subnets. Test RDP and SMB shares for weak credentials or unpatched vulnerabilities (e.g., EternalBlue variants).
   
   
4. Cloud & VPN Testing: Audit split-tunnel configurations to confirm whether traffic bypasses corporate inspection. Examine cloud-IAM roles for over-privileged accounts.

This step-by-step internal pentest guide for remote work uncovers both technical and configuration weaknesses across distributed environments.

Step 4: Simulating Insider Threats & Lateral Movement

• Privilege Escalation: Exploit known flaws such as CVE-2020-1472 (Zerologon) or unpatched Windows Print Spooler bugs to gain domain-admin access.
  
  
• Pass-the-Hash & Token Theft: Capture and reuse NTLM hashes or Kerberos tickets to move laterally across endpoints.
  
  
• Cloud Misuse: Test abuse of overly broad AWS IAM policies or Azure AD conditional access gaps.
  
  
• Credential Harvesting: Simulate phishing campaigns targeting remote staff, then use harvested credentials to breach internal assets.

How do you simulate insider threats remotely?

Use compromised credentials within your VPN session to emulate lateral-movement tactics, testing multi-factor bypass and privilege misuse.

Step 5: Analyzing Findings & Prioritizing COVID-19 Era Vulnerabilities

1. Risk Scoring: Map each finding to a CVSS score and business-impact rating.
   
   
2. Threat Modeling: Combine scan results with real-world attack scenarios—e.g., exfiltration through Shadow IT or cloud service abuse.
   
   
3. Prioritization Matrix: Focus on high-severity issues affecting VPN gateways, unpatched RDP endpoints, and misconfigured cloud buckets.
   
   
4. COVID-19 Remote Internal Pentesting Best Practices: Emphasize rapid remediation of remote-access flaws, enforce zero-trust micro-segmentation, and validate employee training.

By correlating technical data with operational risks, you create a targeted remediation roadmap.

Step 6: Reporting, Compliance & Next Steps (PCI DSS & ISO 27001)

• Executive Summary: Present key risks and business impact in clear, non-technical language.
  
  
• Technical Appendices: Detail methodology, tools used, and raw findings for the SOC and IT teams.
  
  
• PCI DSS 11.3.1 Mapping: Document how your internal pentest meets the requirement for quarterly testing of in-scope systems.
  
  
• ISO 27001 Controls: Reference A.12.6.1 (technical vulnerability management) and A.9.2.3 (management of privileged access).
  
  
• Remediation Roadmap: Provide step-by-step guidance—patch schedules, configuration changes, and follow-up validation tests.

A well-structured report accelerates executive buy-in and compliance sign-off.

Step 7: Continuous Monitoring & Retesting for Long-Term Security

• Regular Scans & Pentests: Schedule automated vulnerability scans weekly and full internal pentests quarterly.
  
  
• Integration with SIEM: Stream live VPN, RDP and cloud-API logs into your security platform to catch anomalous behavior.
  
  
• Patch Verification: After each patch cycle, run targeted scans to validate fixes.
  
  
• Internal Network Assessment Program: Treat internal testing as an ongoing security pillar—just like firewall rule reviews or antivirus updates.
  
  

Ongoing validation ensures your distributed security posture keeps pace with remote-work changes.

Conclusion

As hybrid and remote models persist, internal penetration testing must evolve to cover home networks, VPNs, and cloud estates. Following this step-by-step roadmap—complete with People Also Ask insights, AI overview guidance, and compliance tie-ins—you can safeguard your distributed workforce against modern threats.

Book a Pentest Today