Around this same time last year, many of us said our final goodbyes to Windows XP and Exchange 2003. This year, Microsoft’s latest End-Of-Life (EOL) event – along with good sense – will force most of the firms that are still using Windows Server 2003 to replace it with a newer version of the Windows Server operating system (OS). July 14th, 2015 marks the end of extended support for the 2003 product line – after that date, there won’t be any more security updates.
For those unfamiliar with the issue this raises, compliance regulation and standards related to private information and security dictate that firms must keep up-to-date with regular patches to the software and hardware that powers their businesses. Your firm’s Written Information Security Program (WISP) should detail a policy of adherence to these standards, among many others, and in there somewhere you have almost certainly indicated that you are keeping your systems updated with respect to security.
Like Windows XP, Windows Server 2003 has been around long enough and really should be replaced, so there is not much point in delaying the switch. Most firms have likely changed over to Windows Server 2008 or 2012, but those that haven’t made the change yet should be planning on upgrading their server(s) in Q2 of 2015.
Alternatives to Windows 2003?
Assuming your firm is committed to Microsoft Server products, you have two choices:
1. Windows Server 2008 r2 (2008)
2008 is a mature operating system, which is still in use at a large number of firms today. However, mainstream support for 2008 ended earlier this year (1/13/2015), and though extended support is available until 1/14/2020, it probably doesn’t make sense to move from 2003 to 2008 in 2015. Firms that have existing 2008 software licenses may not want to incur the additional expense of 2012 licenses, and those with significant compatibility concerns may opt to install Windows 2008 on new server hardware.
2. Windows Server 2012 r2 (2012)
2012 is the latest and greatest from Microsoft. It has a shiny new interface and a bevy of neat features like deduplication. My experience with 2012 has been overwhelmingly positive. Though worries about 2012 compatibility with legacy applications may delay widespread acceptance of this operating system, many firms will ultimately choose to make the switch to 2012.
What happens if we stay on Windows 2003?
Your server will still work, but you will not get any more security updates from Microsoft, and your firm will technically be out of compliance.
What else could happen?
Software companies and other parties your firm interfaces with will assume that you are making these updates. Your firm’s failure to upgrade to a later version of Windows Server could cause problems that you and your staff may not be able to anticipate.
As an example of this, one of my clients that was slow to upgrade all of their Windows XP systems last year found that the latest version of Orion’s desktop software, which was automatically updated sometime in Q1 of 2014, was incompatible with Windows XP. Unfortunately for the client, there wasn’t a way to reverse the update or use an older version.
At the time, I was surprised, especially because the customer wasn’t given any notice of the “feature enhancement.” It didn’t make sense that a software company would launch an update incompatible with existing customer desktops that were still supported by Microsoft. Thankfully, Orion addressed the issue quickly by providing the users affected with remote desktop (RDP) connections to Orion servers for an interim period.
About the Author: Kevin Shea is the Founder and Principal 
Consultant of Quartare; Quartare provides a wide variety of technology solutions to investment management and financial services firms nationwide.
For details, please visit Quartare.com, contact Kevin Shea via phone at 617-720-3400 x202 or e-mail at kshea@quartare.com.