The Great Windows Server 2003 migration: Where do we go from here?

Pick the right path


We all have to move away from Server 2003 before it turns into a pumpkin in July, but there are so many options out there that choosing the destination for our data and workloads can be a little overwhelming.

What your workloads are will play a big part in determining which operating system you can upgrade to. The details of your financial and licensing situations also play a part. Choosing what to migrate to – especially with things down to the wire like this – is frustrating, complicated and stressful.

Let's see if we can remove some of the uncertainty.

Pastures new

The options for migration are Linux, BSD and the cloud. If you are an organisation which has left Server 2003 migrations this late, then there are really only a few circumstances in which migrating to a non-traditional option is possible.

The first circumstance is where you have a workload for which the existing vendor has provided a migration path. For example, we could be talking about an old financials package where the latest greatest is in the cloud: QuickBooks is an example that comes to mind.

If all you were doing was basic file sharing, you could get a NAS and use it instead. Choices range from Synology NASes for SMBs all the way up to industry powerhouses such as NetApp filers.

Of course, there is a reason why people use Windows Server as a file server. It integrates well with Microsoft's own Active Directory (among many other offerings), and to be perfectly blunt Windows Server makes a heck of a good file server on its own. Choose wisely, and take the time to check out all the neat file server features of Server 2012 R2.

If you were using Server 2003 only for some really basic networking features, there is probably no good reason to keep on using Windows in this role.

While DNS should probably be handled by your domain controller (at least in part), DHCP, VPN access, firewalls intrusion detection and so on work great from Linux, BSD or any of thousands of switches, routers and other hardware appliances.

You might move certain websites off Windows and over to Linux, BSD or to a cloud service provider. It makes sense to investigate this if those websites are coded in languages such as PHP or Python that use third-party intepreters installed on Windows, especially if you are using Apache on Windows instead of IIS.

For every other case, though, it is probably not worth the hassle. You will probably find migrating from Windows to Linux involves rather a lot more trouble than the cost of a new Windows licence is worth.

So basic file serving might be a reason to move from Server 2003 to something non-traditional. Networking and network security could be put forward as a good reason to move. Some websites under some circumstances, maybe. The list of workloads where is makes sense to move from Server 2003 to something that is not Windows is not overwhelming.

More Windows

Most people who are migrating workloads off Server 2003 will be moving to another version of Windows. Sadly, it is not quite so simple as just picking the newest version and off you go. While this will work for most workloads, it certainly won't work for all, nor is it always the best fit even when possible.

Consider for a moment that many organisations still rely on 16bit applications. There is only one migration path available for these workloads and that is Server 2008 x86. No Server 2008 R2, no Server 2012.

And just as we are hitting end of support for Server 2003 in July, Server 2008 hits the wall in January 2020. Systems administrators running those workloads may have a difficult migration ahead of them.

There are many applications that won't make the jump all the way from Server 2003 to Server 2012 R2. This may be because they rely on some component or library that isn't available under Server 2012 R2, or because they rely on some undocumented feature, bug or a dated security model which had been fixed by the time Server 2012 R2 came out.

In that case, it is worth checking to see if Server 2008 or Server 2008 R2 will work, for now. That will solve the immediate problem of Server 2003 passing out of support, but not the more long-term problem that when Server 2008 or Server 2008 R2 turn into a pumpkin in 2020 you are back on the migration treadmill, this time without a viable destination.

For most workloads, however, there should be no problem in simply installing them on Server 2012 R2 and having them work. If your workloads will work on Server 2008, 2008 R2, 2012 and 2012 R2, which do you choose? The answer is Server 2012 R2, but not for the reasons Microsoft will tell you.

Top of the class

Cast your mind back for a moment to 2003: public cloud was not really a thing, convergence was all about getting telecoms firms to run data, and Facebook and other social media giants were unborn. In other words, 12 years is as heck of a long time in IT.

When Server 2012 first came out, I wrote a piece on the 10 best Server 2012 features. All of these are, of course, included as part of Server 2012 R2, but Server 2012 R2 has other benefits that are worth considering as well.

Top of my list is storage tiering. If you are using Windows Server as a file server you are probably using Storage Spaces to handle your disks and SSDs. With storage tiering you can use SSDs to accelerate a pool of traditional magnetic storage, gaining a dramatic speed boost for very little additional cost.

Along with this is storage pinning – the ability to pin files or folders to a specific tier of storage – and write back cache – the ability to use an SSD to accelerate your system even when Storage Spaces is not directly managing your pool of traditional disks. These are much overlooked but very important features of Server 2012 R2.

Networking enhancements in Server 2012 R2 are another overlooked gem

Hyper-V and failover clustering enhancements are also worth a mention. I realise that many people upgrading from Server 2003 will be using hypervisors from other companies, but for those who are Hyper-V shops or coming from bare metal, it is really worth looking at how far both Hyper-V and failover clustering have come. Microsoft really did a great job in both areas on this release of Windows.

Networking enhancements in Server 2012 R2 are another overlooked gem. VPN services (both site-to-site and user-to-site) have been updated to be multi-tenant capable. Originally designed for service providers and enterprises, this does make a big difference for SMBs with multiple sites. For those with higher-end internet connections, BGP support for Windows is big news.

Remote Desktop Services (the evolution of Terminal Services) also got a much needed overhaul. The most critical feature is session shadowing: the ability for an administrator to take over a desktop with the user still connected so that the administrator can make changes with the user watching.

There are many other features worth exploring, but I think the overall message is clear. Unless you have a workload that simply won't work on Server 2012 R2, Microsoft's latest server operating system should be the target for the workloads you are moving off Server 2003.

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