Advanced Penetration Testing Guide
Professional Scenario: Penetration Testing for a Mid-Sized Financial
Institution
Engagement Overview:
The objective is to assess the security posture of a mid-sized financial institution's IT
infrastructure, focusing on Active Directory, web applications, Office 365, and social media
accounts. The engagement will follow a comprehensive methodology to identify
vulnerabilities and provide actionable remediation strategies.
Scope Overview
1. Active Directory Compliance Review
o AD Vulnerability Assessment
o Hardening and Policies Review
o Azure AD Review
2. Vulnerability Assessment
o Web Servers (5 servers with 8 portals)
o Internal Servers (40 servers)
o Pen Testing of 5 Web Servers
3. Office 365 Compliance Test
o Microsoft Defender Policy Review and Hardening
o Microsoft Office 365 Exchange Server Review
o Improving Microsoft 365 Security Score
4. Social Media Accounts and Critical Systems Audit
o Vulnerability Assessment and Testing
1. Active Directory Compliance Review
AD Vulnerability Assessment
Tools: PowerView, BloodHound, ADRecon, Mimikatz
Steps:
1. Initial Reconnaissance:
o Use PowerView to identify domain trusts, users, and group memberships:
powershell
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Import-Module PowerView
Get-NetDomain
Get-NetGroup -GroupName "Domain Admins"
2. Analyze with BloodHound:
o Collect data with BloodHound and visualize attack paths:
bash
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bloodhound-python -d <domain> -u <username> -p <password>
3. Use ADRecon:
o Execute ADRecon to gather a comprehensive report:
bash
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.\ADRecon.ps1 -Domain <domain>
4. Credential Dumping with Mimikatz:
o Utilize Mimikatz to extract plaintext passwords and hashes from memory
(requires proper authorization):
powershell
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sekurlsa::minidump <dump_file>
sekurlsa::sekurlsa
Hardening and Policies Review
Tools: Microsoft Security Compliance Toolkit, Group Policy Management Console (GPMC),
Local Security Policy
Steps:
1. Review GPOs:
o Analyze Group Policies for compliance with best practices.
2. Utilize Security Compliance Toolkit:
o Download and apply security baselines for Windows Server and Windows 10.
3. Local Security Policy Review:
o Check local security settings on servers to ensure alignment with
organizational policies.
Azure AD Review
Tools: Azure AD PowerShell Module, Azure Security Center
Steps:
1. Audit Azure AD:
o Use PowerShell to review roles and permissions:
powershell
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Get-AzureADDirectoryRole
2. Evaluate Security Center:
o Review alerts and recommendations for Azure resources in the Azure Security
Center.
2. Vulnerability Assessment
Web and Internal Servers Assessment
Tools: Nmap, Nessus, Acunetix, OpenVAS, Burp Suite, Nikto
Steps:
1. Network Scanning with Nmap:
o Conduct a stealth scan to identify live hosts:
bash
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nmap -sP 192.168.1.0/24
2. Vulnerability Scanning with Nessus:
o Set up and run a detailed scan targeting web and internal servers.
o Review the detailed report for vulnerabilities, focusing on high and critical
risks.
3. Web Application Testing with Acunetix:
o Configure Acunetix to perform a thorough scan of all web applications.
o Utilize the "Authenticate" feature for protected areas and analyze the results.
4. Advanced Scanning with OpenVAS:
o Create and execute a new scan with OpenVAS, focusing on the latest CVEs.
bash
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openvas-start
5. Web Application Testing with Burp Suite:
o Intercept traffic and test for vulnerabilities using the scanner.
o Manually explore the application using the Intruder and Repeater tools for
more targeted tests.
6. Nikto for Web Server Scanning:
o Use Nikto to identify potential misconfigurations and outdated software:
bash
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nikto -h http://target.com
Penetration Testing of Web Servers
Tools: Metasploit, SQLMap, Raccoon Stealer, OWASP ZAP
Steps:
1. Exploit Vulnerabilities with Metasploit:
o Identify vulnerabilities and select appropriate exploit modules.
bash
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msfconsole
search <vulnerability>
use <exploit>
2. SQL Injection Testing with SQLMap:
o Perform automated SQL injection testing on identified endpoints:
bash
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sqlmap -u "http://target.com/page.php?id=1" --risk=3 --level=5 --dump
3. Credential Harvesting with Raccoon Stealer:
o (Only in authorized scenarios) Simulate an attack to test credential protection
mechanisms.
4. OWASP ZAP for Web Application Security:
o Use OWASP ZAP to scan web applications for vulnerabilities, including XSS
and CSRF:
bash
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zap.sh -quickurl http://target.com
3. Office 365 Compliance Test
Microsoft Defender Policy Review
Tools: Microsoft 365 Defender, Compliance Center
Steps:
1. Review Microsoft Defender Policies:
o Check for potential misconfigurations and hardening recommendations in
Microsoft 365 Defender.
2. Audit Compliance Center:
o Use the Compliance Center to review DLP policies and ensure sensitive data
protection.
Exchange Server Review
Tools: Exchange Management Shell, PowerShell, Security & Compliance Center
Steps:
1. Connect and Review Mail Flow:
powershell
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$UserCredential = Get-Credential
Connect-ExchangeOnline -Credential $UserCredential
Get-TransportRule
2. Evaluate Security Settings:
o Review mailbox audit settings and DLP policies.
Improving Microsoft 365 Security Score
Steps:
1. Access Security Center:
o Analyze the security score and implement the suggested recommendations to
improve overall security.
2. Regular Training:
o Conduct user awareness training based on the results from phishing
simulations and other security assessments.
4. Social Media Accounts and Critical Systems Audit
Vulnerability Assessment
Tools: Hootsuite, Social Media Security Tools, Nmap
Steps:
1. Audit Social Media Accounts:
o Use Hootsuite to review permissions and assess third-party app integrations.
2. Network Scanning:
o Use Nmap to scan any associated infrastructure:
bash
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nmap -sS -p- <IP>
3. Social Media Penetration Testing:
o Simulate social engineering attacks to test user awareness and account
security.
4. Document Findings:
o Create a detailed report on vulnerabilities and provide remediation
recommendations.
