IT Freedom Blog

Ditching Windows Server 2003

by Matt Miller on

Like it or not, end of life for Windows Server 2003 is quickly approaching. The day of reckoning is July 14, 2015, at which point critical security updates and support will no longer be available for those choosing to stick with Windows Server 2003. The idea of shifting to a newer version of Windows Server like 2008 R2 or 2012 may be disconcerting for some, but without security patches protecting against evolving threats to network security and data compromise, sticking with Server 2003 is no longer an option for responsibly-managed networks. Although the transition process may seem nerve wracking, it is possible to enjoy a seamless move from Windows Server 2003 to Windows Server 2012 R2.


Get started early and keep the following suggestions in mind as you update your server:

 32 and 64-Bit Platforms

At one time, 32-bit platforms were the standard in the computing world. Essentially, “32-bit” refers to the size of the addresses used for memory storage. (Think street numbers: streets with more houses need more numerals in the address numbers.) Storage capacity has since increased, with new servers featuring memory addresses with widths of 64 bits.

Although 64-bit processors compatible with Windows Server 2003 have been available for quite some time, their 32-bit predecessors remain quite common, and most all instances of Windows Server 2003 are of the 32-bit variety regardless of the underlying hardware. Many Windows Server 2003 users fear that their current 32-bit applications may not be compatible with newer versions of Windows such as Windows Server 2008 R2, 2012, and 2012 R2, which only come in 64-bit versions. Shifting old applications to new servers can be can be a challenging undertaking, and the same approach doesn’t work for all situations. It’s best to let a qualified IT provider who’s well-versed in making the shift identify the right solution and guide you through it.

Taking On The Cloud

Looking at the upgrade from Windows Server 2003 to newer versions of Windows is also a perfect time to consider migrating some or all server-based services and applications to cloud-based solutions. Below are the cloud migrations we’d recommend tackling first and a few considerations to have when making the shift:


Email is a ubiquitous and cloud-friendly service these days, so it’s a natural choice for small and medium-sized organizations looking to move to the cloud to start by moving from an on-site email server to a cloud-based service.

When moving email from your own server to a cloud-based solution like Office 365 or Google Apps, keep in mind that you may have to change email clients, such as from Outlook to a browser. Cloud-based email services offer some great features that aren’t always available in on-premise email setups, such as two-factor authentication for security purposes. This means that after entering your username and password, you’ll receive a unique code on another device (or, in some cases, on app on that same device), that you’ll then enter as your second credential. Be sure to enable two-factor authentication on your account settings, as it’s often not the default.


The aforementioned Office 365 and Google Apps solutions also include file storage/sharing services—OneDrive and Google Drive, respectively—to which businesses might move file shares. When moving files from a local server to a web-based provider like OneDrive, Google Drive, Dropbox, or, be aware that sharing behaviors may change, so you’ll want to work through workflow changes with your staff and IT department to ensure a smooth transition.


Moving servers wholesale to an infrastructure-as-a-service (IaaS) platform like Amazon Web Services is also an option for those organizations that want or need to run their own applications on server instances that they maintain directly, but don’t want the associated cost of buying and physically hosting hardware. IaaS platforms like AWS or Microsoft Azure essentially rent virtual servers running on hardware that they own and maintain, abstracting away the physical realities of dealing with server hardware. It’s important to note that using IaaS platforms can be in some ways more technically challenging than buying dedicated hardware, so this option is best used for financial reasons or to address challenges like geographic redundancy versus reducing technical complexity.

Look For Special Perks

Microsoft aims to make the switch from WS 2003 to WS 2012 R2 as easy as possible. For some organizations, this means extra encouragement in the form of free or inexpensive use of essential applications, such as Office 365 as mentioned above. Office 365 is available at greatly reduced costs to non-profit organizations, and some versions come with MS Office suite licenses that can further reduce costs and simplify license tracking and management.

Similarly, one of Google’s efforts to ease and incentivize the transition to the cloud comes in the form of Google Apps, such as Google Apps for Work, which nonprofit organizations can obtain access to for free. For organizations that are mostly limited to file sharing, email, and other common applications, Google Apps is potentially capable of reducing both the hassle and expense related to WS 2012 R2 migration by eliminating the need for dedicated servers entirely, and thus, would be a worthwhile investment even if it wasn't offered at no cost.

Small businesses that do need to maintain a dedicated server for whatever reason may want to consider taking advantage of offerings such as Windows Server 2012 Essentials, which is intended for simplified installation, migration, and long-term management in small to mid-size businesses.

The era of Windows Server 2003 is quickly drawing to a close. For the stubborn business clinging to this outdated operating system, it is finally time to acknowledge that migration to modern versions of Windows Server is inevitable. Avoid the urge to procrastinate and, instead, start crafting a detailed migration plan. If you need a helping hand during the transition process, feel free to contact us. IT Freedom will guide you through the ins and outs of WS 2003 migration, delivering you to the wonderful world of WS 2012 R2 in one piece.

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