Windows enumeration is the process of systematically gathering information about a Windows system or network. This includes details about users, groups, shares, services, installed applications, network configurations, and more. Enumeration is typically performed after initial access is gained, but it can also be part of a reconnaissance phase in ethical hacking.

The goal is to identify potential vulnerabilities, misconfigurations, and escalation paths that could be exploited by attackers. Effective enumeration is critical for understanding the security posture of a Windows environment.

Enumeration is a key phase in the MITRE ATT&CK framework and is essential for ethical hacking engagements. By enumerating Windows systems, ethical hackers can:

• Identify privilege escalation opportunities
• Discover sensitive data and misconfigured shares
• Map out network topology and trust relationships
• Assess security controls and patch levels
• Simulate real-world attacker behavior for risk assessment

According to the CISA, improper configuration and lack of visibility are among the top causes of security breaches in Windows environments. Enumeration helps uncover these weaknesses before malicious actors do. For a deeper dive into the latest techniques, check out this Password Cracking Guide 2025: 5 Latest Techniques.

Ethical hacking must always be conducted within the boundaries of the law and with explicit authorization. Before performing any enumeration:

• Obtain written permission from the system owner
• Define the scope and rules of engagement
• Comply with relevant laws and regulations (e.g., GDPR, ISO/IEC 27001)
• Follow ethical guidelines from organizations like OffSec and ISACA

Unauthorized enumeration is illegal and unethical. Always act responsibly to protect privacy and data integrity. For practical advice on staying compliant, review Legal Password Testing: Stay Compliant in 2025.

A variety of tools are available for Windows enumeration, including both built-in utilities and third-party applications. Key resources include:

• Command Prompt and PowerShell
• Sysinternals Suite (Microsoft Docs)
• Third-party tools like enum4linux, WinPEAS, and PowerView
• Automated scripts and frameworks (e.g., PowerSploit)

Ensure your environment is isolated (e.g., using virtual machines) and that you have backups before proceeding.

Start by collecting fundamental system details. The systeminfo command provides a comprehensive overview:

systeminfo

This reveals OS version, architecture, hotfixes, and more. To retrieve the hostname:

hostname

Alternatively, use:

echo %COMPUTERNAME%

Identifying the exact Windows version and build is crucial for vulnerability assessment. Use:

ver
wmic os get Caption,CSDVersion,Version,BuildNumber

For PowerShell:

Get-ComputerInfo | Select-Object WindowsProductName, WindowsVersion, OsBuildNumber

Enumerate local users and groups to identify potential targets and privilege escalation paths:

net user
net localgroup
net localgroup Administrators
wmic useraccount get name,sid,status

For PowerShell:

Get-LocalUser
Get-LocalGroup
Get-LocalGroupMember -Group "Administrators"

Understanding network interfaces and routing is essential for lateral movement and network mapping:

ipconfig /all
route print

PowerShell alternative:

Get-NetIPAddress
Get-NetRoute

Check firewall status and rules:

netsh advfirewall show allprofiles
netsh firewall show state
netsh firewall show config

Enumerate network shares:

net share
Get-SmbShare

For more on securing and auditing network shares, see NTLM Hash Cracking: Modern Techniques 2025.

List active network connections and listening ports:

netstat -ano
Get-NetTCPConnection
Get-NetUDPEndpoint

This helps identify running services and potential remote access points.

Enumerate all running and stopped services:

sc query
sc query type= service state= all
Get-Service

To get detailed service configuration:

sc qc [ServiceName]
Get-WmiObject win32_service | Select-Object Name, State, PathName, StartMode

List installed programs to identify vulnerable or outdated software:

wmic product get name,version
Get-WmiObject -Class Win32_Product | Select-Object Name, Version

For a more comprehensive list, check the registry:

reg query HKLM\Software\Microsoft\Windows\CurrentVersion\Uninstall
reg query HKLM\Software\WOW6432Node\Microsoft\Windows\CurrentVersion\Uninstall

Enumerate scheduled tasks, which may reveal persistence mechanisms or sensitive scripts:

schtasks /query /fo LIST /v
Get-ScheduledTask | Select-Object TaskName, TaskPath, State

Reiterate user and group enumeration for privilege analysis:

net user
net localgroup
Get-LocalUser
Get-LocalGroup

Review password policies to assess account security:

net accounts
Get-LocalUser | Select-Object Name, PasswordNeverExpires, PasswordRequired

Check account lockout policy:

net accounts
secedit /export /cfg C:\secpol.cfg
find "Lockout" C:\secpol.cfg

For best practices on password policy and testing, see Password Policy Best Practices 2025.

Identify potential privilege escalation vectors:

• Unquoted service paths (MITRE ATT&CK T1574.009)
• Weak service permissions
• AlwaysInstallElevated registry keys
• DLL hijacking opportunities

Automated tools like WinPEAS and Seatbelt can help identify these issues.

Look for sensitive files in common directories:

• C:\Users\Public\
• C:\Users\<username>\Documents\
• C:\Windows\System32\config\
• C:\ProgramData\

Use:

dir /s /b C:\*.txt
dir /s /b C:\*.xml
dir /s /b C:\*.config

Reveal hidden and system files:

dir /a:h /s C:\
dir /a:s /s C:\

PowerShell alternative:

Get-ChildItem -Path C:\ -Hidden -Recurse -ErrorAction SilentlyContinue

Review file and directory permissions to identify weak ACLs:

icacls "C:\Path\To\FileOrFolder"
Get-Acl -Path "C:\Path\To\FileOrFolder"

Key registry hives for enumeration:

• HKEY_LOCAL_MACHINE (HKLM)
• HKEY_CURRENT_USER (HKCU)
• HKEY_USERS (HKU)

Enumerate keys:

reg query HKLM
reg query HKCU

Check for stored credentials in the registry:

reg query "HKLM\SECURITY\Policy\Secrets"
reg query "HKCU\Software\Microsoft\Windows\CurrentVersion\Run"

Also review credential managers and password vaults.

Enumerate auto-start programs for persistence mechanisms:

reg query "HKLM\Software\Microsoft\Windows\CurrentVersion\Run"
reg query "HKCU\Software\Microsoft\Windows\CurrentVersion\Run"
wmic startup get caption,command

List all shared folders:

net share
Get-SmbShare

From a remote system, use:

net view \\target_ip
smbclient -L \\target_ip -N

Access shares:

net use \\target_ip\sharename
smbclient //target_ip/sharename -U username

Enumerate permissions and contents to identify sensitive data.

Null sessions allow unauthenticated access to certain Windows resources. To test for null sessions:

net use \\target_ip\ipc$ "" /u:""
enum4linux -a target_ip

Note: Modern Windows systems restrict null sessions, but misconfigurations may still exist.

Enumerate domain users and groups:

net user /domain
net group /domain
Get-ADUser -Filter *
Get-ADGroup -Filter *

Requires appropriate privileges and PowerShell Active Directory module. For step-by-step details, see How to Extract Hashes (eg: NTLM, Kerberos) from Windows Systems.

List and review GPOs for security settings and misconfigurations:

gpresult /R /Scope:User
gpresult /R /Scope:Computer
Get-GPO -All

GPOs can reveal password policies, login scripts, and more.

Identify domain trusts for lateral movement opportunities:

nltest /domain_trusts
Get-ADTrust -Filter *

Trust relationships can expand the attack surface across multiple domains.

• net (user, group, share, view, accounts)
• systeminfo
• wmic
• PowerShell cmdlets
• sc (service control)
• reg (registry queries)
• tasklist, taskkill
• ipconfig, route, netstat

• Sysinternals Suite
• WinPEAS
• PowerSploit
• PowerView
• enum4linux-ng
• Seatbelt
• Nmap (with NSE scripts)
• ldapdomaindump

• WinPEAS (privilege escalation checks)
• PowerSploit (PowerShell exploitation framework)
• PowerView (domain enumeration)
• enum4linux-ng (SMB and RPC enumeration)

Automated scripts accelerate the enumeration process and help uncover subtle misconfigurations.

• Document everything: Keep detailed notes and screenshots for reporting and remediation.
• Check permissions: Always verify your access level before running enumeration commands.
• Be stealthy: Use non-intrusive methods to avoid detection by security tools.
• Correlate findings: Combine data from multiple sources for a comprehensive view.
• Watch for false positives: Not all findings are exploitable; validate before reporting.
• Respect privacy: Do not access or disclose sensitive data unless authorized.

Common pitfalls include overlooking hidden files, misinterpreting permissions, and failing to review scheduled tasks or registry auto-start entries.

• Is Windows enumeration legal? Only with explicit authorization and within the defined scope of an engagement.
• Can enumeration be detected? Yes, especially if using noisy tools. Use stealthy, built-in commands where possible.
• What is the difference between enumeration and exploitation? Enumeration is information gathering; exploitation involves taking advantage of vulnerabilities.
• Which tools are best for beginners? Start with built-in Windows tools and gradually explore third-party utilities like WinPEAS and PowerView.
• How often should enumeration be performed? Regularly, as part of vulnerability assessments and after significant system changes.

• MITRE ATT&CK: Windows Techniques
• CISA Cybersecurity Advisories
• OWASP Top Ten
• SANS Institute: Windows Enumeration Techniques
• Microsoft Sysinternals Suite
• OffSec: Penetration Testing Resources
• ISACA: Security Resources
• Password Recovery Tools 2025: Top Picks Ranked

Windows enumeration is a critical skill for ethical hackers, penetration testers, and security professionals. By mastering the techniques and tools outlined in this Windows Enumeration Cheat Sheet 2025, you can effectively identify vulnerabilities, assess risk, and help organizations strengthen their security posture. Always operate within legal and ethical boundaries, document your findings, and stay updated on the latest enumeration methods and defensive strategies. For further learning, consult the authoritative resources listed above and practice in safe, controlled environments.