Microsoft Server 2003: The End of an Era

On July 14, 2015 Microsoft will cease to support or issue any security updates for Windows Server 2003. That means if your customers continue to run their Windows Server 2003 environment after this date they are going to be opening themselves to potentially disastrous security threats.

Upgrade your MS2003 Server

This end-of-life event offers the perfect opportunity for you to help guide your customers into the next phase of their business technology plan. Are they ready to migrate to the cloud? Is an upgrade to Microsoft Office 365 a better fit for them? Would they prefer to invest in a new server altogether?

Your customers will be looking to you for guidance and advice on their next steps. Here we lay out the four options you should start discussing with your customers today.


  • Do Nothing.

    To be clear, your customers do not have to make a move or migration by July 14. Their server and the applications that run on it will still work for the time being (though functionality will start to decrease down the road). The main concern here is that they will be exposing themselves to possibly devasting security threats. However, if they are hosting a custom application on the server that does not require internet access, their risk will be relatively low and they may not feel the need to make a move right now.

  • Upgrade to Windows Server 2012.

    For customers who don’t trust the cloud, this is their ‘best’ option. It comes as no surprise that some IT professionals are more comfortable managing their own server in their own environment. With an upgrade to Server 2012, these customers will maintain the same on-prem server environment they had before. On the flip side, investing in a new server can get expensive with each individual license, not to mention the amount of time, money, and manpower that will be necessary to manage, update, and support the server in-house.

  • Move to a Hosted Server Solution.

    This is your customers’ most future-proof solution by far. With a hosted server solution the provider takes on the task of updating the software. This is a huge benefit as running server updates can be extremely time consuming. In the long term, moving their server to hosted environment will lessen your customers’ costs of operation and will offer the added benefit of running on an OPEX cost model as opposed to a CAPEX model. It’s also a highly scalable solution with the ability to add new users and services at just the click of a button. Keep in mind, one of the downsides of moving to a hosted environment is the loss of in-house control and accountability. Organizations that have a lot of interdependencies and integrations may also want to avoid a hosted solution because integrating some of these systems can be extremely complicated and time consuming. Additionally, when moving to a hosted environment your customers will need to increase their bandwidth and while this presents an additional revenue opportunity for you, it may very well be seen as a disadvantage to your customers.

  • Update to Office 365.

    If your customers are running only Exchange on their Server 2003, an upgrade to Office 365 is the way to go. Licensing for the product is subscription-based which makes it a scalable and flexible option. Your customers only pay for what’s live and that number can change from month to month. It is also extremely affordable with the all-in cost starting at around $20 a month per license. Additional services can be purchased a la carte so your customers can mix and match Microsoft products in any combination at any time. It is worthwhile to note that while a Microsoft Office 365 sale doesn’t have great margins, it does offer a valuable opportunity for you to start the cloud conversation with your customer.​

As with all major decisions, there are advantages and disadvantages to each of the options listed above. The important thing is to communicate these options with your customers laying out the pros and cons of each, so you can help them make an informed and strategic decision about their technology.

Looking for another way to start the conversation?

Take a look at our Windows Server 2003 End of Life Discovery Questions here.

About the Author
Dave Landsberger is a sales trainer at TBI. He designs content and delivers sales training to support TBI’s sales campaigns. Dave develops training programs that foster a culture of continuous learning to ensure the maximum effectiveness of TBI’s sales efforts. You can contact Dave at or connect with him on LinkedIn.