Why 1.6 million people will miss Microsoft's Windows Server 2003 date with fate

You want to do what? Again?!

Upgraded your Windows Server 2003 yet? Don’t worry, you’re not alone.

Gartner reckons there are eight million Windows Server 2003 OS instances in operation, and SI Avanade reckons that of those instances, a full 20 per cent – 1.6 million – will blow past the 14 July end-of-support date.

What happens six months from now, on 14 July? That's the date Microsoft issues its last security fix ever for Window Server 2003 – the end of extended support from the server operating system's maker.

That means any new hacks built or vulnerabilities discovered in Windows Server 2003 and those running the legacy server OS will be facing them on their own.

It’s a problem if your server systems hold data of any kind – which they will – and could be accessed directly or indirectly from the internet.

Server systems are generally thought isolated from external attackers, but last year’s attack on Sony Pictures put an end to that illusion.

Sony’s internal financial and employee systems were compromised and employees’ personal data snaffled by hackers. Sony’s only response was to take the systems offline.

This becomes of even greater concern if you work in a regulated industry like finance or pharmaceutical, where watchdogs will levy fines if you put customers’ data at risk.

The last time we jumped though this upgrade hoop was in April 2014, when Microsoft ended extended support for Windows XP.

XP had been running on millions of machines worldwide, tens of thousands in the UK government alone.

Of course the number of Windows Server 2003 instances is small in comparison to the numbers of Windows XP overall, but the problem is actually bigger.

A 2013 survey of Fortune 1000 IT pros by AppZero, touted by Microsoft, reckons more than half had 100 or more Windows 2003 servers.

Windows Servers run systems that are the beating heart of organisations - ERP, finance, accounting, manufacturing and more.

The consensus among those The Reg has spoken with is that despite the mission-criticality of Windows Server systems, people are holding off moving.

Aidan Finn is technical sales lead for value-added reseller MicroWarehouse and a Microsoft MVP.

He coaches and trains partners who work with end users on implementing Microsoft technologies. An expert on Windows Server and Windows Server virtualisation, Finn admits to a sense of unease on the topic of moving off Windows Server 2003.

"When I look at the kind of people that have this issue, it's not just companies that tend to be under-funded, low skilled or slow to do things, it's every kind of company – including extremely well-funded, very leading edge IT organisations. It is businesses from the smallest to the largest, it's evenly spread around the planet and industry segments."

“When I talk to people, they are pretty non-committal about upgrades,” Finn told The Reg just before Christmas. “I have a feeling of unease about it, that come January, February and March I expect there will be a lot or work happening and a lot of pressure.”

Application migration specialist Camwood is jittery, too. The firm was busy on Windows XP upgrades and had about 10 Windows Server 2003 projects currently underway when we spoke.

Camwood solutions architect Ed Shepley told us: “We had a fairly decent flurry from people when [end of support] was announced for Windows XP.

“We were kept quite busy before XP and expected a similar pace for Server 2003 but we found people have a different challenge.”

Nick East, chief executive of IT provider Zynstra, told The Reg that 50 to 60 per cent of customers who have contacted his firm about migration are still only at the talking stage.

Just a small fraction have finished, with about 10 to 20 per cent “on the journey", he said.

All of which is a problem, because according to Gartner, the “typical” migration runs between nine to 15 months – from research to upgrade, test and rollout.

Translation: if you haven’t started now, you won’t make July’s deadline.

Given the importance of such systems, why aren’t people moving sooner? One problem is the sheer complexity and importance of the systems we're talking about. The workloads on Windows Server 2003 are the really big thorny ones. Email servers, web hosting or file serving have likely already been migrated to Windows Server 2008 R2. The hard stuff is what’s left – which firms seem to have been putting off.

One such example is a specific line-of-business app running on SQL Server on Windows Server 2003 for a particular vertical sector – with plug-ins to ERP and CRM that are also tied to the customer.

East draws a picture: “Such a system will have been super reliable and has been running in the business for some time and its bound up with everything – ordering, logistics, supply, customer support and perhaps there’s no good way to move it into the cloud. Then, perhaps, there are applications that are integrated to lots of other things in the business; you move one part and you have to move lots of other processes, too.”

Complicated and critical by their nature, these systems have only grown in complexity during the 15 years of Windows Server 2003’s life.

Throw out the yardstick

A difficult migration project by any normal yardstick is made harder by step change in systems architectures – from 32-bit Windows Server 2003 to 64-bit Windows Server 2012. Further, since Windows Server 2003, Microsoft has put Hyper-V in the server software for free, introducing possible new opportunities in virtualisation.

IT departments are also facing kickback and delay from the business side of the house in terms of securing the pounds and pence required to finance the change.

Another upgrade, just over a year after Windows XP? On systems that are out of sight of the average business user? IT departments likely found getting approval and budget for Windows XP hard enough – and that was right in the faces of most of those who were responsible for OKing such projects.

Gartner vice president and distinguished analyst Carl Claunch said: "When I look at the kind of people that have this issue, it's not just companies that tend to be under-funded, low-skilled or slow to do things – it's every kind of company, including extremely well-funded, very leading edge IT organisations. It is businesses from the smallest to the largest, it's evenly spread around the planet and industry segments."

There’s a firm consensus there will be a late rush as July’s date approaches. And you won’t see wholesale server estates migrate, but rather specific apps say insiders.

Finn predicts movement as the support deadline enters the six-month time frame and people realise there’s no way out.

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