Windows Server 2003–R.I.P. (soon)

imageAs I write this post, there is only around 300 days left for Windows Server 2003 life. Yes, time goes by fast and we have to embrace the future. It was a good run. When Server 2003 came by, I remember that some of new features and capabilities were awesome. Maybe it happens to all new operating systems. But at some point, technology evolves and you are faced with the challenge of upgrading your environment. Windows 2008 is here for the last 6 years. Window Server 2012, now R2, is already around for a couple of years. It is a lot to grasp, of course. New versions come faster every time and the new possibilities are immense. You don’t have to embrace all new features at once. It is known that OS upgrades are like painting a plane on the fly, so, buckle up!

For starters, it is not like Windows 2003 will stop working. In fact, if it was time-bombed, this would be much easier task. A few important facts are important though and should not be taken lightly. As of July 14th, 2015, Windows Server 2003 won’t have any support. That means (1) that there won’t be any updates. In 2013 only, while Server 2003 was under extended support, 37 security updates were released. It also means (2) that you won’t be compliant with any standards or regulations. Therefore, making business with companies that demand those regulations, like PCI with VISA/Mastercard won’t be an option. That can be a dramatic situation for an organization. More than that, (3) you can run, but you cannot hide. Every edition, virtual or not, SMB or enterprise will be affected. There is no safe haven.

So, it is time to act. Start planning. Luckily, current technologies, although it might feel challenging, bring a great deal of options to replace Windows Server 2003 in your corporation. Windows Server 2012 R2 and its greatly rich set of features allows for a lot of flexibility and easier usage when thinking of on-premises approaches. On the other side, you have Microsoft Azure, which is a new compute model and also brings an incredible set of options for your migration. And of course, you can always use the best of both worlds: go hybrid. Extend your datacenter and leverage your existing infrastructure along with an infinitely extendable datacenter in the cloud.

Among other features, Windows Server 2012 R2 offers enhancement in the Storage Area, Network virtualization, Automation, Identity management and many others. Azure, the same way, offers storage options, with amazing redundancy capabilities and performance, at prices that can be hardly matched by on-premises implementations. Besides that, it is an extensible technology, where you can if your dynamic or static needs, creating virtual machines, websites, load-balancer sets, very quickly or in an automated fashion, without having to worry about which BIOS, Storage Driver or which firmware are in place. It is there, available, for you to use. Of course, it is a different model, including on the pricing side, and it has to be tested and understood.

In order to migrate your Windows 2003 ecosystem, start first (1) by assessing what you have in your environment. It is easy to fight an enemy when you know its size. Identify applications, their owners, locations, etc. For that you can leverage many tools, including the Microsoft Assessment and Planning Tookkit (MAP). Second (2), look at these applications in terms of how critical they are, what type of technology they use (IIS, MMC, ASP, .NET, etc.) and how complex they are. You may be surprised to find some applications that are critical, but not too complex, which would make them very good candidates to start the process. Step three (3) is a very interesting one: choose your destination: where should you move this applications to? As I have mentioned before, Window Server 2012 R2, on-premises, might seem like a good and logical option. However, there is a lot more that can be done. For example, you could, instead of spinning up a new Hyper-V cluster with Server 2012 R2, you could connect you datacenter to Microsoft Azure and spin the virtual machines there, without a single drop of sweat or blood in the datacenter. Depending on the application, IIS based, for example, you could even just move into an Azure WebSite offer in Azure and don’t even care about the virtual machines themselves. Or a bit of both. Additionally, when you think Exchange, for example, you could use Office 365, the same way you could pick Lync Online or SharePoint Online.

In this process, some hard decisions will have to be made. You may find some 3rd Party custom applications that simply won’t work in 2012 R2 or Azure. Or 32 bits vs. 64 bits (although it is usually not a big deal). You may need to either re-develop, adapt, replace or, if you are luck and can, drop it).

Once you have the migration matrix in place, plan to start as soon as the business allows you to. The time is short and your critical business application should be exposed to new vulnerabilities and shouldn’t either be the cause for not being able to do business with other great corporation due to the lack of compliance. It is time to that Windows Server 2003 for the good times together and let it rest in peace.

Please make sure to review some of the links below to help you with the process:

Migrating to Windows Server 2012 Training

Transforming the Datacenter

Virtualizing Your Data Center with Hyper-V and System Center

Licensing Windows Server 2012 R2


Hope this helps!