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Windows Server 2003 Migration Guide: Choosing a Replacement OS

Microsoft is putting Windows Server 2003 out to pasture on July 14, 2015. As the server operating system goes end-of-life, Microsoft will drop support and stop issuing security and other patches. Many third-party application providers will stop supporting the platform as well. Continuing to rely on Windows Server 2003 will put your business at risk of falling out of compliance with regulations such as HIPAA and PCI. It's pretty clear that you need to migrate away from Windows Server 2003.

In the first part in this series, we provided a methodology for planning and executing a successful migration. In this article, we'll talk about your options for migration and how to choose the right platform.

Your choice of platform will be dictated by the way your organization is currently using Windows Server 2003. Optimize your IT operation by taking a comprehensive hardware and software inventory, understanding how it is being used, and reprovisioning it to a more efficient platform—whether that's physical, virtual, or cloud. Your current architecture may not be the best way to serve applications to your users. For example, that custom application on SQL Server on Windows Server 2003 could now be ported to run in the cloud on Azure. Understanding what you've got along with your options will let you turn Windows Server 2003's demise into an opportunity instead of a crisis.

Weighing Your Migration Options

Staying Inside the Windows World
If you are wedded to the Microsoft ecosystem, then your most straightforward option is to migrate to Windows Server 2012 R2. A good place to start gathering information is with the Microsoft's Windows Server 2003 Migration Planning Assistant. Another good resource is the Microsoft Assessment and Planning Toolkit. The latter will also help you migrate from SQL Server 2005, which will reach the end of its life on April 12, 2016.

The first step is cataloging your Windows servers and their roles. You need to know if it's being used as a file server, a Web server, an application server, or for Active Directory or Terminal Services, to figure out how to replace it with Windows Server 2012 R2. You also need to know if you're running other applications such as SQL Server, Exchange Server, or SharePoint Server along with any other custom or third-party applications.

You then have to choose whether to run Windows Server 2012 R2 on dedicated physical hardware or on a virtual machine. If you run on a virtual machine then you can run your Windows Server 2012 R2 instance within your datacenter or in the cloud. If you have multiple physical Windows Server 2003 servers, then you might consider migrating one of them to Windows Server 2012 R2 on some beefy hardware and consolidating the rest to Windows Server 2012 R2 Hyper-V virtual machines running on top of that.

Making the Move to Linux
If you don't have custom applications that require the Microsoft platform, now might be a good time to make the switch to a small business Linux server. A few of the more popular Linux small business server alternatives include Univention Corporate Server, the Zentyal SMB Edition, and Igaware Small Business Server. You might also consider building a Linux server from scratch using a server distribution from Ubuntu, Fedora or CentOS. If you want to move away from Microsoft Exchange, then consider Linux-based Exchange alternatives such as Scalix, Sogo, or Zarafa.

The key to a successful Linux migration is pulling it off without users noticing a difference. They should be able to map drives, read email, and schedule meetings the same way they could before, within the Microsoft ecosystem. However, if you rely on SQL Server or SharePoint, you won't find alternatives that let you have a transparent migration. There are Linux-based alternatives to both of these platforms, but the migration would be a challenge.

Considering the Cloud
Depending on the role of your existing Windows Server 2003, you may need to break up the functions and set up different cloud services to replace it.

Microsoft Azure Virtual Machines can host applications, databases, and Web servers, and you can connect over a VPN for greater security. Be careful when migrating because you're changing systems architecture, as opposed to moving the whole stack to a new server. Things won't be as straightforward as when everything ran on the same machine, but you gain the benefits of lower up-front costs and increased scalability that comes with switching to the cloud. A typical migration must include application and data analysis, application migration, data migration, testing and optimization, and operation and management. Plan how you're going to manage the change in architecture, and be sure to give yourself some extra time to get used to the differences between running the whole stack on an on-premise server and in the cloud.

If you rely on your Windows Server 2003 mainly for file storage, then you can use Microsoft Azure Storage and include a local StorSimple device for a tiered storage strategy. If you're a small business, then you might want to consider cloud document storage solutions like Box, Dropbox, Google Drive, or OneDrive, where you will gain simplicity at the cost of control and flexibility.

If you're running Microsoft Exchange for email and calendaring, then you can replace it with a hosted Exchange service such as Microsoft's Exchange Online. You can also use Office 365 for hosted Office, Exchange, SharePoint, and Lync applications. You can even leave Microsoft's fold completely with Google Apps or try the new WorkMail, Amazon's cloud email service for businesses with full support for Outlook.

So Many Choices, So Little Time
Whichever path you chose in migrating from Windows Server 2003, you're running out of time. Unsupported servers are not something you want, unless you're looking for reasons to lie awake in bed at night. Assess your existing systems and explore your options. Turn this migration into an opportunity to update systems architecture and make your IT operations more efficient.

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