Over the last few months I have done quite a few sessions on Windows Server 2003 and this has invariably ended in some interesting conversations which I thought I would write up now I have a few days in front of a desk. The objections to upgrading generally fall into three categories which I would summarise as:
- There is no problem we’ll just pay for extended support
- There is no budget and no perceived value to the business
- Legacy applications aren’t supported on Windows Server 2012R2
Let’s look at each of these in turn:
Pay for extended Support
This is at best an expensive stop gap – it just buys you time to migrate. So all that means for me is that you’ll come back to this post in two years time or whenever and then carry on reading!
We have no resources to do the upgrade
I would argue that one of the reason you have no spare capacity in your IT department is precisely because you are running Windows Server 2003. It was designed in an age where each IT pro was probably responsible for just a handful of server making it hard to manage at scale like later versions. E.g. remote WMI is not turned on and there’s no PowerShell (which some of you might think is a good thing 
).
So how to move off it when you are maxxed out? Hopefully it’s already virtualised giving you some management benefits and the ability to checkpoint/snapshot it when applying changes in case things break. I guess the question is what are those servers doing? If they are running infrastructure (file servers, domain controllers DHCP etc.) then there are huge advantages in moving these off to windows server for little or no work – granted AD might be more tricky if you have heavily modified schemas.
Any of these will make a compelling business case which I’ll get to in a minute but the problem here is typically the applications running on these old servers. If it’s Microsoft stuff (Exchange, SharePoint, SQL Server) then the cloud makes a lot of sense unless you have a clear reason to keep these services close to you.
So I see many business upgrading Exchange & SharePoint to office 365 especially in education and organisations with a large remote workforce as corporate data is traversing the internet anyway so why not store it there? This would then give the bandwidth to go after the harder to shift applications running on Windows Server 2003. SQL Server 2000/2005 should be easy to upgrade and I have a few posts on my blog about the SQL Server Upgrade Advisor to help with that.
My legacy applications aren’t supported on Windows Server 2012 R2
Having got the easier stuff out of the way you are probably left with websites and non-Microsoft workloads. I don’t have an easy answer for you but do remember that if the OS is not going to be supported in future then by association those applications won’t have support either so you’ll need to work out what the risks and benefits are of these older systems with the business owner and possibly carry on with them until there is a case to replace them. This is not perfect but what you will have done by now is get your data centre into far better shape.
There’s no business justification to upgrade
If you have played with Windows Server 2012 /R2 you’ll be able to articulate this better than I can. If I think about how efficient the current release in using hardware from storage deduplication, to SMB3 storage to effective networking (NIC teaming IP address management etc.) then these should all mean you can run more workloads on a given infrastructure even if you haven’t adopted Hyper-V yet. However my go-to feature would be multi server management either with Server Manager, PowerShell or the addition of System Center. If we then rely on managing servers form a central point we can remove the management tools from each of them to make them yet more efficient and cut in half the patching they need. Trust me this will give you tangible time back in your day to do the job you are paid for (supporting the business) rather than fire fighting.
I realise all of this is easy say sitting in a nice Microsoft office which is worlds away from your production environment so I have a challenge and an opportunity for you. Why not take a day out of your office and come and talk to us about this and learn about how to get the most of your data centre at the same time. We are hanging out at the Excel Centre next Wednesday (12th November) at an event called Future Decoded. There a dedicated data centre track with sessions on Windows Server 2003 and what’s in the new one (the Windows Server Technical Preview) run by expert MVPs and technical Microsoft staff, the session is called Modernize, Transform and Extend your Datacentre to the Cloud with sessions starting from 13:45 (GMT time). These guys will be around all day to field questions, so bring us your past and we’ll explain the future
Will you be coming to Modernize, Transform and Extend your Datacentre to the Cloud sessions? If so what are you most looking forward to? Let us know in the comments section below or via @TechNetUK.