Exploiting and Learning: A Dive into CVE-2008–4250 on Day 31 of My Cybersecurity Journey

Nisha P
Women in Technology
3 min readDec 10, 2023

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In this post, I’ll share my experience using Metasploit to compromise a vulnerable Windows XP machine, known as Legacy, on Hack the Box, by exploiting the notorious CVE-2008–4250.

Understanding CVE-2008–4250

Before diving into the details of my exploit, let’s unpack what CVE-2008–4250 is. This vulnerability is a significant security flaw in Microsoft Windows operating systems, particularly affecting the Server service that manages file and printer sharing. The core issue lies in how Windows handles network services, allowing an attacker to send specially crafted network packets to execute arbitrary code remotely. In simpler terms, this vulnerability could enable an attacker to take control of a system without the user’s knowledge.

https://nvd.nist.gov/vuln/detail/cve-2008-4250

My Approach with Metasploit

Using the powerful penetration testing tool, Metasploit, I set my sights on Legacy, a machine running a vulnerable version of Windows XP. The machine, part of the Hack the Box platform, was an ideal candidate to demonstrate the practical implications of CVE-2008–4250.

Nmap scan reveals that Legacy is a Windows XP box running SMB services

The process involved exploiting the vulnerability to gain unauthorized access to the Legacy machine. This hands-on experience highlighted the severity of the vulnerability and the ease with which an unpatched system could be compromised.

Search for Metasploit module that applies to Windows XP and SMB
Running the Metasploit module

You can read more information about the ms08_067_netapi exploit here.

Accessing the Administrator profile to capture the root flag

The Mitigation: MS08–067

The adventure wouldn’t be complete without discussing the mitigation of this vulnerability. Microsoft released a security update, MS08–067, to patch this critical flaw. This update was crucial for Windows 2000, XP, Vista, and Windows Server 2003 and 2008 users, addressing the vulnerable component in the Server service to prevent such remote exploits.

https://learn.microsoft.com/en-us/security-updates/securitybulletins/2008/ms08-067

My exploration of Legacy was more than a successful exploit; it served as a stark reminder of the importance of regular system updates and security patches. MS08–067, though released years ago, still stands as a testament to the ongoing battle against cyber threats and the need for constant vigilance in cybersecurity.

Stay tuned as I continue to navigate through the diverse challenges and learning experiences in my #100DaysofCybersecurity challenge. The journey is far from over, and there’s much more to learn and discover in the realm of cybersecurity!

Connect with me on LinkedIn: https://www.linkedin.com/in/nishaprudhomme/

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