FreeIPA Penetration Testing Methodology
A comprehensive guide on how to conduct a structured and thorough penetration test of FreeIPA deployments.
Ethical Use Only
FreeIPA Penetration Testing Methodology Overview
1. Pre-Engagement
Scoping, planning, and information gathering
2. Reconnaissance & Enumeration
Identifying targets and gathering information
3. Vulnerability Assessment & Exploitation
Finding and exploiting vulnerabilities
4. Reporting & Remediation
Documenting findings and providing solutions
Pre-Engagement
The pre-engagement phase is critical for establishing the scope, rules of engagement, and expectations for the penetration test. This phase ensures that all parties understand what will be tested, how it will be tested, and what the deliverables will be.
Scoping and Planning
Proper scoping is essential for a successful penetration test. It defines the boundaries of the test and ensures that all parties have a clear understanding of what will be tested.
Target Systems
- FreeIPA servers (primary and replicas)
- Client systems enrolled in the FreeIPA domain
- Supporting infrastructure (DNS, NTP, etc.)
- Web interfaces and APIs
Testing Boundaries
- IP ranges and domains in scope
- Systems explicitly out of scope
- Testing hours and blackout periods
- Permitted testing techniques
- Prohibited activities (e.g., DoS attacks)
Testing Approach
- Black box (no prior knowledge)
- Grey box (limited knowledge)
- White box (full knowledge and access)
- Internal vs. external perspective
Rules of Engagement
The rules of engagement document outlines the agreed-upon parameters for the penetration test. This document should be signed by all parties before testing begins.
Essential Components
- Contact information for all parties
- Emergency contacts and escalation procedures
- Detailed scope of testing
- Testing schedule and timeline
- Permitted testing techniques and tools
- Reporting requirements and deadlines
- Data handling and confidentiality agreements
Information Gathering
Before beginning the technical assessment, gather as much information as possible about the target FreeIPA environment. This information will help guide your testing approach.
Environment Information
- FreeIPA version and deployment architecture
- Number of servers and their roles (primary, replicas)
- Operating system versions and patch levels
- Network architecture and segmentation
- Integration with other systems (e.g., Active Directory)
Security Controls
- Authentication mechanisms in use
- Access control policies
- Network security controls (firewalls, IDS/IPS)
- Monitoring and logging capabilities
- Previous security assessments or known issues
Case Study: Pre-Engagement for Enterprise FreeIPA Assessment
In a recent engagement with a large financial institution, the pre-engagement phase revealed critical information that shaped the entire assessment. The organization had a complex FreeIPA deployment with multiple replicas across different geographic locations.
Key Findings During Pre-Engagement:
- The primary FreeIPA server was running version 4.8.0, which had known vulnerabilities
- Integration with an external Active Directory forest created additional attack vectors
- Custom applications were using the FreeIPA API for authentication
- Previous security assessments had identified issues that remained unresolved
This information allowed the penetration testing team to focus their efforts on the most vulnerable components and tailor their approach to the specific environment.
Reconnaissance
The reconnaissance phase involves gathering information about the target FreeIPA environment without directly interacting with the systems. This phase helps identify potential entry points and targets for further testing.
Passive Reconnaissance
Passive reconnaissance involves gathering information without directly interacting with the target systems. This can help identify potential entry points and targets for further testing.
OSINT (Open Source Intelligence)
- Search for public information about the organization's infrastructure
- Check for leaked credentials or sensitive information
- Review public code repositories for configuration information
- Examine job postings for technology stack details
DNS Analysis
- Identify domain names associated with the organization
- Look for FreeIPA-related subdomains (e.g., ipa.example.com)
- Check for DNS SRV records that might reveal FreeIPA services
- Example command:
dig SRV _ldap._tcp.example.com
Active Reconnaissance
Active reconnaissance involves directly interacting with the target systems to gather information. This phase helps identify FreeIPA servers and services.
Network Scanning
- Scan for hosts running FreeIPA-related services
- Identify open ports associated with FreeIPA (389/636, 88/464, 80/443, 53)
- Example command:
nmap -sV -p 389,636,88,464,53,80,443 <target_range>
Service Identification
- Identify FreeIPA web interfaces
- Confirm LDAP and Kerberos services
- Check for version information in service banners
- Example command:
nmap -sV --script="ldap* and not brute" <target_ip>
Reconnaissance Documentation
Document all findings from the reconnaissance phase, including:
- Identified FreeIPA servers and their IP addresses
- Open ports and running services
- Version information for FreeIPA and related services
- Domain names and DNS configuration
- Web interfaces and their URLs
Enumeration
The enumeration phase involves gathering detailed information about the FreeIPA environment, including users, groups, hosts, and access controls. This phase helps identify potential security weaknesses and targets for exploitation.
Anonymous Enumeration
Start by attempting to enumerate information without authentication. FreeIPA may expose some information to unauthenticated users.
LDAP Anonymous Binding
- Attempt anonymous LDAP binds to gather information
- Example command:
ldapsearch -x -h <target_ip> -b "dc=example,dc=com" -s base - Look for naming contexts and directory information
Web Interface Analysis
- Examine the FreeIPA login page for version information
- Check for information disclosure in error messages
- Look for publicly accessible API endpoints
- Example command:
curl -k https://<target_ip>/ipa/ui/
Authenticated Enumeration
If you have valid credentials, use them to gather more detailed information about the FreeIPA environment. This can be done using both LDAP queries and the FreeIPA CLI.
User Enumeration
- Enumerate users and their attributes
- Example command:
ldapsearch -x -h <target_ip> -D "uid=user,cn=users,cn=accounts,dc=example,dc=com" -w password -b "cn=users,cn=accounts,dc=example,dc=com" "(objectClass=posixAccount)" - Look for privileged users and service accounts
Group Enumeration
- Enumerate groups and their members
- Example command:
ldapsearch -x -h <target_ip> -D "uid=user,cn=users,cn=accounts,dc=example,dc=com" -w password -b "cn=groups,cn=accounts,dc=example,dc=com" "(objectClass=posixGroup)" - Focus on administrative and privileged groups
Host Enumeration
- Enumerate hosts and host groups
- Example command:
ldapsearch -x -h <target_ip> -D "uid=user,cn=users,cn=accounts,dc=example,dc=com" -w password -b "cn=computers,cn=accounts,dc=example,dc=com" "(objectClass=*)" - Identify critical servers and potential lateral movement targets
Access Control Enumeration
- Enumerate HBAC rules and sudo rules
- Example command:
ldapsearch -x -h <target_ip> -D "uid=user,cn=users,cn=accounts,dc=example,dc=com" -w password -b "cn=hbac,dc=example,dc=com" "(objectClass=*)" - Look for overly permissive rules or misconfigurations
Enumeration Documentation
Document all findings from the enumeration phase, including:
- Users, groups, and their relationships
- Privileged accounts and service accounts
- Hosts and host groups
- HBAC rules and sudo rules
- Role-based access control configuration
- Password policies and account lockout settings
Vulnerability Assessment
The vulnerability assessment phase involves identifying potential security weaknesses in the FreeIPA environment. This includes checking for known vulnerabilities, misconfigurations, and weak security controls.
Version and Patch Analysis
Check the FreeIPA version and patch level to identify known vulnerabilities that might affect the environment.
Version Identification
- Check the web interface for version information
- Use authenticated commands:
ipa --version - Check package versions on the server:
rpm -q freeipa-server
CVE Mapping
- Map the identified version to known CVEs
- Check the CVE database for applicable vulnerabilities
- Prioritize vulnerabilities based on CVSS score and exploitability
Configuration Analysis
Analyze the FreeIPA configuration to identify security misconfigurations and weaknesses.
Authentication Configuration
- Check password policy settings
- Example command:
ipa pwpolicy-show - Look for weak password requirements or missing account lockout settings
- Check for Kerberos pre-authentication settings
Access Control Configuration
- Analyze HBAC rules for overly permissive settings
- Check sudo rules for privilege escalation paths
- Review role-based access control configuration
- Look for misconfigured self-service permissions
TLS/SSL Configuration
- Check for weak cipher suites or protocols
- Example command:
nmap --script ssl-enum-ciphers -p 443 <target_ip> - Verify certificate validity and trust chain
- Check for certificate management misconfigurations
Vulnerability Prioritization
Prioritize identified vulnerabilities based on their potential impact and exploitability.
| Priority | Criteria | Examples |
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| Low |
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Vulnerability Documentation
Document all identified vulnerabilities, including:
- Vulnerability description and affected components
- CVE reference (if applicable)
- CVSS score and severity rating
- Potential impact if exploited
- Evidence of the vulnerability (screenshots, command output)
- Recommended remediation steps
Exploitation
The exploitation phase involves attempting to exploit identified vulnerabilities to demonstrate their impact. This phase should be conducted with caution and only with explicit authorization.
Caution
Authentication Attacks
Attempt to bypass or compromise authentication mechanisms to gain unauthorized access to the FreeIPA environment.
Password Attacks
- Password spraying against common accounts
- Brute force attacks (if allowed by rules of engagement)
- Example command:
hydra -l admin -P wordlist.txt ldap://<target_ip> - Note: Be cautious of account lockout policies
Kerberos Attacks
- Kerberoasting to extract service account hashes
- Example command:
GetUserSPNs.py -dc-ip <target_ip> <domain>/<user>:<password> -request - AS-REP Roasting for accounts with pre-authentication disabled
- Example command:
GetNPUsers.py <domain>/ -usersfile users.txt -format hashcat -outputfile hashes.txt
Authentication Bypass
- Test for CVE-2020-10747 (WebUI authentication bypass)
- Check for LDAP injection vulnerabilities in authentication forms
Exploiting Known Vulnerabilities
Leverage known vulnerabilities in FreeIPA or related components to gain unauthorized access or escalate privileges.
CVE-Based Exploitation
- Research available exploits for identified CVEs
- Use exploit frameworks like Metasploit or custom scripts
- Example: Exploiting CVE-2020-10747 (if applicable)
LDAP Injection
- Test for LDAP injection vulnerabilities in web interfaces or APIs
- Craft malicious LDAP queries to bypass authentication or extract sensitive information
- Example:
ldapsearch -x -H ldap://<target_ip> -b "dc=example,dc=com" -D "uid=*)(|(uid=*))" -w ""
Privilege Escalation
- Exploit misconfigured sudo rules to gain root access
- Leverage HBAC rules to gain unauthorized access to systems
- Example:
sudo -u root <vulnerable_command>
Exploitation Documentation
Document all successful exploitation attempts, including:
- Vulnerability exploited and affected components
- Exploitation method and tools used
- Credentials or access gained
- Impact of the exploitation
- Screenshots and command output
Post-Exploitation
The post-exploitation phase involves gathering additional information and maintaining access to the compromised FreeIPA environment. This phase helps demonstrate the full impact of the vulnerabilities.
Information Gathering
Gather additional information about the compromised environment to identify sensitive data and potential lateral movement targets.
Credential Harvesting
- Search for stored credentials in configuration files
- Dump Kerberos tickets and hashes
- Example:
klist -kte - Extract credentials from memory
Data Discovery
- Identify sensitive data stored in the FreeIPA environment
- Search for personally identifiable information (PII)
- Locate confidential documents and files
Network Mapping
- Map the internal network to identify potential lateral movement targets
- Identify other systems integrated with FreeIPA
- Example:
ip route
Maintaining Access
Establish persistent access to the compromised FreeIPA environment.
Backdoor Accounts
- Create new administrative accounts
- Modify existing accounts to grant administrative privileges
- Example:
ipa user-add backdoor --first=Backdoor --last=User --email=backdoor@example.com --password
Service Modifications
- Modify system services to execute malicious code
- Create scheduled tasks to maintain access
- Example:
systemctl edit sshd.service
SSH Keys
- Install SSH keys for persistent access
- Example:
echo "ssh-rsa AAAAB3Nz... user@example.com" >> /home/user/.ssh/authorized_keys
Post-Exploitation Documentation
Document all post-exploitation activities, including:
- Credentials harvested
- Sensitive data discovered
- Network map and lateral movement targets
- Persistence mechanisms established
- Impact of the compromise
Reporting
The reporting phase involves documenting all findings from the penetration test and providing recommendations for remediation.
Report Structure
A well-structured report is essential for communicating the findings of the penetration test to the client.
Executive Summary
- Brief overview of the penetration test
- Summary of key findings and recommendations
- Overall security posture assessment
Scope and Methodology
- Description of the scope of the penetration test
- Explanation of the methodology used
- Rules of engagement and limitations
Findings and Recommendations
- Detailed description of each vulnerability
- Evidence of the vulnerability (screenshots, command output)
- CVSS score and severity rating
- Potential impact if exploited
- Recommended remediation steps
Conclusion
- Summary of the overall security posture
- Recommendations for improving security
- Suggestions for future testing
Report Content
The report should include detailed information about each vulnerability identified during the penetration test.
Vulnerability Description
Provide a clear and concise description of the vulnerability.
Evidence
Include screenshots, command output, and other evidence to support the findings.
Impact
Explain the potential impact of the vulnerability if exploited.
Remediation
Provide detailed recommendations for remediating the vulnerability.
Reporting Best Practices
- Use clear and concise language
- Provide detailed evidence to support findings
- Prioritize vulnerabilities based on impact and exploitability
- Offer practical and actionable remediation recommendations
- Tailor the report to the audience
Remediation
The remediation phase involves implementing the recommendations provided in the penetration test report to address the identified vulnerabilities.
Remediation Planning
Develop a remediation plan to address the identified vulnerabilities in a systematic and prioritized manner.
Prioritize Vulnerabilities
- Focus on critical and high-severity vulnerabilities first
- Consider the potential impact and exploitability of each vulnerability
Develop Remediation Strategies
- Identify appropriate remediation techniques for each vulnerability
- Consider the cost and complexity of each remediation option
Implement Remediation Measures
- Apply patches and updates to address known vulnerabilities
- Implement configuration changes to address misconfigurations
- Strengthen authentication and access control mechanisms
Verify Remediation Effectiveness
- Conduct follow-up testing to verify that the vulnerabilities have been remediated
- Use automated scanning tools to identify any remaining vulnerabilities
Remediation Techniques
Implement specific remediation techniques to address the identified vulnerabilities.
Patching and Updates
- Apply the latest security patches and updates to FreeIPA and related components
- Use a patch management system to automate the patching process
Configuration Hardening
- Strengthen password policies and account lockout settings
- Disable unnecessary services and features
- Implement strong access control policies
Network Security Controls
- Implement firewalls and intrusion detection/prevention systems
- Segment the network to limit the impact of a potential breach
- Monitor network traffic for suspicious activity
Remediation Documentation
Document all remediation activities, including:
- Vulnerabilities remediated
- Remediation techniques used
- Dates of remediation
- Verification results