Moving on: preparing for Windows Server 2003 end of support

End of support for Windows Server 2003 is just around the corner. Simon Bisson examines the options

By Guest on 05 June 2015
Moving on: preparing for Windows Server 2003 end of support

Last summer’s end of support for Windows XP was a wake-up call for many businesses. The venerable desktop OS was no longer supported, unless you were willing to pay Microsoft a hefty fee. 2015 sees another workhorse Microsoft product reaching its end-of-support deadline, namely Windows Server 2003. If you are managing servers that run Windows Server 2003, then you need to circle 14 July 2015 on all your calendars in the biggest and reddest pen you have.

Desktops are the visible face of business computing. But they’re not the backbone of the information systems that power our companies. That’s the role of the server, sitting there in a machine room or a data centre – or even in a humble closet – managing our data, our e-mail, and keeping those desktop PCs managed and running. Making sure you’re ready for Windows Server 2003’s end of support is going to be critical for your business, as there are big risks involved in managing a migration, moving not just server roles and services, but also applications and files.

End of support for servers is not something that can be ignored. If your servers aren’t supported, then you’re not just at risk of security exploits; you’re also at risk of being out of compliance with the terms of your business insurance, and with corporate and government

Microsoft’s documentation makes it abundantly clear: there’s no safe haven for businesses that decide not to migrate away from Windows Server 2003. Once the deadline passes there will be no security updates and no support – not even for virtualised instances. You’ll be on your own, shouldering all the risk of running out-of-date code.

Do an inventory
The process of moving away from Windows Server 2003 will be much like any other server migration. The only real difference is that there’s a hard deadline, and very real risks to your business that can result from failing to meet it. And, like other server migrations, the underlying problem is that, once set up and running, servers are left for months or even years under desks and in data centres. They’re not glamourous, like desktops and laptops: they are workhorses that we don’t notice until something goes wrong.

Your first task is to create an inventory of every server in your organisation, determining the OS version it’s running, its hardware specification, the software that it’s running and the data that it’s storing. You’ll also need to inventory and document your current Active Directory, including details of the servers that are running key roles. While some documentation splits this phase into discovery and assessment, the process of creating an inventory combines both approaches into a single operation.

An inventory like this is the heart of any migration plan as it allows you to determine the priority for each server, and helps define the migration path for key applications and data. There’s plenty of tooling available for this phase, including free software from Microsoft. Armed with a software inventory you can now determine the available options. You can check out the upgrade paths offered by your vendors, and the costs associated with upgrades. You can also see what versions of Windows Server you can upgrade to – whether you can only go to the next version, so passing the problem a little further down the line, or whether you’re able to go straight to the latest release – Windows Server 2012 R2.

However you decide to proceed, you have plenty of options. Modern server software is much more flexible and powerful than its 2003 predecessors. It takes advantage of the latest networking and hardware capabilities, as well as the benefits you get from combining cloud services with on premise servers.

While replacing Windows Server 2003 is essential, it’s also an opportunity to rethink your network architecture and to start to take advantage of new tools and services. You can start by upgrading hardware, and then looking at how you can take advantage of cloud services to increase your options.

The modern world
The obvious upgrade for Windows Server 2003 is the latest Windows Server release – Windows Server 2012 R2 (the next release is due in 2016). It’s a considerable advance on Windows Server 2003, with support for hardware virtualisation and for high density storage using off-the-shelf disks and enclosures.

To get the most from a new OS, you do need up-to-date hardware. Drivers for servers that are four, five, or even ten years old are unlikely to have been updated for the latest server releases, and it’s likely you’re going to have to invest in new servers to handle the requirements of a migration.

New hardware isn’t a bad thing, although it could represent a considerable upfront cost if you’ve got a sizable fleet of Windows Server 2003 machines to upgrade. That said, you’re going to get much more ‘bang for your buck’ with the latest Intel-based server hardware: 64-bit processors can access much more memory while the latest multi-socket, multi-core systems are able to handle multiple virtual machines, allowing you to consolidate servers onto fewer physical systems.

Windows system management has changed significantly in the last decade, with a move to using the PowerShell scripting environment to automate much of what used to be manual management tasks. Actions created in Windows GUI controls can be captured in scripts and used as the foundation for programmable system management, where specifics are replaced with generic variables and the resulting scriptlets called as required.

You need to invest in the current generation of Microsoft System Center management tools if you’re taking this approach as these will help you manage and deploy virtual machines that can get the most from your hardware. Making System Center part of your Windows Server 2003 migration also gives you the tooling you need to effectively manage server configurations, as well as controlling your desktop real estate.

Moving to a virtualised environment also lets you take advantage of cloud-based disaster recovery tools, reducing overall risk to your business in the event of a major systems failure. Microsoft has built tools to handle this into its Azure cloud service, which can be used in conjunction with its StorSimple cloud-extended storage arrays.

Going hybrid
Devices like StorSimple are a pointer to a new architecture that is open to you, namely a hybrid cloud. Mixing on-premise servers and cloud services makes a lot of sense, especially when you have to change. Microsoft calls its mix of Windows Server, System Center and Azure platforms the Cloud OS, and there’s a lot to be said for adopting it as a way of upgrading from Windows Server 2003 with minimal capital expenditure. All you need is a nice fast internet connection and you can start mixing and matching cloud with on-site tools. One option is to use the cloud to update your databases, as Azure’s storage and database services are powerful tools that work well with on-premise software and are based on SQL Server technology. If you’re not ready to upgrade on-site SQL Server instances then Azure SQL gives you the opportunity to move to the latest SQL Server features while giving it an on-premise makeover by installing local client software or a web front-end.

You can also use Azure’s high density web servers to manage and host your web content – either via a VPN to an intranet, or across the public internet. The hybrid cloud model goes both ways, and a move to Windows Server 2012 R2 also lets you run Azure-like services on your own servers using the Azure Pack. This adds an Azure-like portal to Windows Server for self-service deployment of virtual machines, as well as supporting Azure’s high density web servers on local Windows Servers.

A cloudy future?
While end of life for a workhorse operating system brings problems, it also brings opportunities. In the process of migrating, you’ll have made an inventory of your server software, and now it’s time to ask yourself just what aspects of it you actually need to run yourself. The last decade has seen an explosion of cloud and software as a service (SaaS) solutions, and a Windows Server 2003 migration might be just the opportunity you need to move some software and services off premises.

That’s going to be even more urgent if you’re running Small Business Server (SBS) 2003, as Microsoft has no direct replacement for its single box server solution. Windows Server 2012 R2 has an Essentials option, which includes some of the client management tools (including agent-based configuration), but it’s closer in concept to the company’s Home Server file and print system. If you’re relying on SBS for SharePoint collaboration and for Exchange e-mail, you’re going to need to consider other options. Cloud solutions like Office 365 will fill much of the gap, offering Exchange, SharePoint and the latest desktop and mobile Office client software. You won’t need to invest in server hardware, or need the same level of support as you’ve needed in the past with on-premise servers, as that’s all handled by Microsoft’s cloud service. However you will need to take into account a change in the way you pay for services: that one-off payment back in 2003 or 2004 will become a recurring monthly per user subscription fee.

There are a lot of advantages to shifting key server functions to the cloud, and not just for applications. Microsoft’s Azure Active Directory is part of its Enterprise Mobility Suite, and extends the familiar Active Directory user management tools to offering controlled single sign-on to many popular cloud services and applications. You can also use it to simplify the process of adding new users, and to revoke access to services when roles change or when users leave the company.

Handing over mundane IT activities to a cloud provider makes a lot of sense. Why do you need to be running a mail server when Microsoft or Google or whoever effectively brings you staff dedicated to running the service? Focusing limited IT budgets on where IT can help your business makes more sense, especially when those IT budgets can be better used to manage BYOD scenarios, or developing new custom business applications. There’s also an accounting benefit, in that it transforms many of the costs involved in IT from capital to operating expenditure.

Rebuilding apps
The hardest part of any Windows Server migration will be rebuilding – or rather, building new – applications. The underlying Windows platform has changed significantly over the last decade, even if much of it still relies on the .NET platform. However, the biggest risk facing application rewrites is that data sources key to the application may well not migrate cleanly, if they migrate at all. That means you should be prepared for the possibility that you will have to completely rewrite all your bespoke applications. At first sight that’s a significant problem, but you can use your server and application inventory to prioritise development, focusing on the most important applications – either in terms of their role in your business workflow, or in terms of their number of users. Understanding what’s needed can help additionally fine tune the redevelopment process, letting you focus on delivering a set of minimum viable products with only the necessary functionality. The opportunity of rewriting core applications doesn’t come along very often, and when it does it comes with the option of re-architecting your business systems. It’s a chance to take advantage of the latest design and development thinking, from micro-services to API-centric development models that give your users the opportunity to create their own apps. It’s also an opportunity to embrace DevOps methodologies and to think about how you might use continuous delivery techniques to deploy application updates with an improved cadence.

What next?
No matter what decisions you make and what path you take, there’s going to be some pain involved in migrating away from Windows Server 2003. Much of that is to do with the sheer age of the OS – it’s more than a decade old. Many applications you use won’t have been updated, and there may not be a migration path to the latest versions for many other critical tools.

But a decade does mean a lot of change, and where in 2003 you had limited options for server roles, the latest technologies mean it’s possible to leapfrog several generations of software and hardware development and end up ahead of your competition. The IT world of 2015 is one where technology is focused on getting the best for your business, whether it be on-premise or in the cloud. Looked at in that light, end-of-support for Windows Server 2003 is most definitely an opportunity for you to change the ways in which you think about and deliver IT.

Just remember that whatever you do, you need to start now. The clock is ticking, and 14 July is not that far away.

Simon Bisson is a technology writer and journalist

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