Windows Server 2003: RIP 2015

In 2014, Microsoft ended support for Windows XP. In 2015, Windows Server 2003 is on the chopping block. Are you ready? Support ends July 14, 2015, which means you need to start planning your transition now.

Why It Matters

Your first question may be, “why does this matter?” If you have an old server running, and it’s completely stable, why mess with it, right? Aside from the obvious – no support – a key reason to upgrade is security.

We’ve had wave after wave of major security exploits this year. In many cases these exploits targeted older technology that was seemingly secure – for example, the HeartBleed bug. If new exploits come out that impact Windows Server 2003, there will be no patch. You will be vulnerable, which means you will be scrambling to upgrade on an emergency basis. If you get hit with a virus that exposes customer information, it could be a public relations nightmare.

Even if your own server doesn’t get hit, performing a server upgrade under those circumstances isn’t likely to go well. Bear in mind that software designed to run on Windows Server 2003 isn’t likely to play nicely with Windows Server 2012 (the current version). That means you’ll have to upgrade your software at the same time you upgrade your server.

A related issue is regulatory compliance. Most regulated industries, like medical or financial, require you to run on supported software. After July 14, 2015, you will be out of compliance and could be subject to penalties.

Your Options

The most obvious solution is to upgrade your server to a newer version. 2012 is the latest, although you can still get the 2008 version through Microsoft’s Volume Licensing Program.

However, you shouldn’t automatically assume a new server is the way to go. If you are running a software applications on an old server, check with your vendor to see if they have a hosted “cloud” version. If they do, consider migrating your software there. Then you can retire the server instead of replacing it.

If it’s running email and sharing files, check out cloud services like Office365 (from Microsoft). You’ll need a fast and reliable internet connection, but this is another case where you may be able to migrate to the cloud instead of replacing an old server.

There is one last option: you can pay Microsoft an exorbitant fee for ongoing support, but it is unbelievably expensive and intended only for large corporations.

If You Upgrade

If you decide to replace your Windows 2003 Server, where do you start? How do you plan?

First, inventory all software applications running on your old servers, so you know what you have to move. For each one, contact the vendor. Find out what has to be upgraded and how to handle migration. Renew your support contracts and be prepared to spend extra for upgrades. Don’t forget to check out training. New versions will likely be more intuitive and more efficient, but your team will need help if the latest version of the software looks completely different from what they use today.

Your worst case situation will be if you have old, custom software, or anything that cannot be upgraded to a new version. If you run into this, consider switching to a new software application that does the same function. It is terribly risky and expensive to keep running on old unsupported software versions, especially when it’s critical to business operations.

Next, check your hardware. If your server is more than four years old, you should upgrade to improve performance and reliability. In most cases it makes sense to virtualize your servers. This means that you use a tool like VMWare or Hyper-V that allows you to install multiple “virtual” servers on one physical server. It’s much like buying a building and having several tenants share the space and resources.

Finally, check your Microsoft software licenses. If you already have some newer servers, it’s possible you are already covered. In a virtual environment, there are a few exceptions but generally one Windows Server license can be used for two virtual servers. If not, you will need a Windows Server 2012 license. You will also need the appropriate number of CALs (client access licenses) which are dependent on the number of users or devices on your network. This is a one-time purchase that applies to the environment overall, so if you add more servers in the future you don’t need more CALs. You only add CALs when you add users or devices. If you are running Microsoft SQL Server, you’ll need to upgrade that as well.

At this point you know what you are migrating, but you still need to create a step-by-step plan. You can set up the new server in advance, but any software migrations will need to be carefully coordinated. Bring in the expertise you need to ensure a smooth transition; otherwise you could experience significant disruption to your business.

If You Move to the Cloud

If you are able to migrate your software to cloud applications, enlist your vendor early on to create a migration plan. The cloud version of your software may have different features that need to be configured, and your team may need training. There will be a data conversion step, where they take your data from the current system and move it into the online version. You’ll normally do this first in a test environment, to make sure it all works. Then you’ll pick a date for the actual migration. This could take an hour or a few days – it just depends on the complexity of your software.

Final Steps

Whether you upgrade or move to the cloud, there’s one last step: retiring your old servers. Turn them off, but keep them around for just a few months. Better safe than sorry – you may find something you missed. After that, have the data on the hard drives destroyed and turn them in for recycling. And enjoy your new applications and the efficiency they bring!


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