Pulling the Plug on Windows Server 2003: Can You Still Manage Your Legacy Systems?

View primer: Managing Your Legacy Systems: What Will Life Be Like After Windows Server 2003?

Last April 2014, Microsoft announced that it will be ending its support for Windows XP. Consequently, a lot of small to large enterprises faced many technological challenges as the systems and servers they relied on for day-to-day operations rapidly approached the end of their supported life. This also meant that their computers were exposed to the risk of unpatched vulnerabilities being exploited. Despite the ended support for the outdated operating system, its market share continued to increase. However, so did the security issues.

[READ: Life After XP]

On July 14, 2015, Windows Server 2003 is set to expire. Microsoft will no longer issue security updates, regular product fixes, and vulnerability notifications for the OS. When this happens, enterprises are encouraged to migrate to newer OSs to protect from system and network exploitation that could result in data breaches, malware infections, and targeted attacks.

The risks of discontinued support

Essentially, when an operating system's extended support ends, security fixes or patches will no longer be available; hence, newly discovered vulnerabilities in the software remain unpatched. Additionally, users and organizations will not be advised of potential vulnerabilities which increase the possibility of being attacked.

In January 2015, Microsoft ended mainstream support for Windows 7 (all editions), Windows server 2008 and 2008 R2, Windows Storage Server 2008, and Microsoft Dynamics C5 2010, NAV 2009, and NAV 2009R2. This marked the point where Microsoft was no longer going to add features to the products but will continue to update with fixes for security and reliability issues—at least until January 14, 2020.

Four key challenges enterprises face when migrating

According to research conducted by Trend Micro, only 35% of businesses have migrated from Windows Server 2003, leaving two-thirds of the 63% to follow suit in the next six months. Based on a joint study by ESG and Trend Micro, 25% of Windows Server 2003 current users will continue to run the OS even without support and maintenance patches. Here the four key challenges:  

1. Migrating entails too much time and effort
2. Legacy applications may not properly run on newer OSs
3. IT teams may not have the expertise to migrate
4. Rewriting applications may not be cost-effective

Facing the next big threat and securing your legacy systems

Given the current threat landscape, where vulnerabilities can endanger an enterprise and the existing challenges that could arise from end-of-life (EOL), we’ve learned that cybercriminals can easily exploit vulnerabilities in systems, servers, applications, including systems that were not previously thought as vulnerable. This shows that migrating from one OS to another may require time and a great amount of effort for a company to upgrade completely.

When Windows Server 2003 reaches its EOL, there won’t be a mechanism to keep it up to date, which is essential in preventing security issues. Pawan Kinger, Director of Deep Security Labs at Trend Micro, warns, “EOL for an OS, specifically for Windows Server 2003, means the beginning of a lot of effort from your IT department’s part. Organizations must prepare to deal with missing security updates, compliance issues, fighting malware, and other non-security related bugs. Users will no longer receive patches for security issues or vulnerability notifications. And they will no longer know when there are vulnerabilities that affect their servers.”  

To protect your systems, you need to assess the risk of the data residing on your servers. If the data isn’t secured by itself, you need to make sure that advanced security controls are in place. This will help maximize the protection for your Windows Server 2003 environment, including intrusion prevention systems, integrity monitoring, and anti-malware solutions. Solutions like Deep Security allow you to monitor any suspicious system changes to your servers using its integrity monitoring capabilities.

Learn more about how you can secure your legacy systems from our the primer Managing Your Legacy Systems: What Will Life Be Like After Windows Server 2003?