While many organisations have made the leap to Windows 7, and increasingly to Windows 8, many remain on Windows XP.
According to Microsoft, a full operating system migration can take up to six months, depending on an organisation's size, so now is the time to act, before the company officially calls time on the operating system on April 8, 2014.
The company also says that it is essential to avoid roadblocks around application compatibility, change management, migration tools, and technical support in order to ensure that time and costs aren't added to the migration process.
There's also the question of which operating system is the best for your organisation, and how you can minimise the risks of continuing to use XP if you miss Microsoft's cut-off date.
ZDNet spoke to industry experts and recent XP émigrés, Campari Australia and the City of Sydney, for advice on making sure your XP migration journey doesn't become an odyssey.
The first issue to tackle any XP migration is a simple and obvious one: Do you move to Windows 7 or Windows 8? The answer, Michael A Silver, VP distinguished analyst at Gartner, says, comes down to two factors: Risk and mobility.
"Windows 7 has been shipping for four years, it is stable, it is well supported by applications, third-party service providers know it, can service it pretty well, and can do migrations," he said. "The migration will be quicker and lower risk when moving to Win 7."
But for organisations with a high need for tablet PCs, or those wanting to future proof their organisations, Windows 8 is a viable choice, Silver says.
"If there are specific benefits you will get, Windows 8.1 is a fine choice," he said. "And for a lot of organisations, it is worth considering 8.1 to avoid this end-of-life migration issue for some time into the future."
Silver does, however, caution organisations that are already underway in their Windows 7 migrations not to stop to ponder adopting Windows 8. In all likelihood, this will introduce potential new costs and delays, and risk the organisation not being off XP by the April cut-off date, as well as potentially leaving the organisation to manage and support two new operating systems instead of one.
For some organisations, the need to migrate off Windows XP might seem like a good opportunity to move off Windows altogether and onto an Apple or Google Chrome-like operating system. Either approach has its risks, Silver advises.
"Today, typically half a given organisation's applications require Windows," he said. "If you had a group of users which didn't require Windows, or you are serving apps to them through something like Citrix XenApp or Remote Desktop Services, certainly, you may have the capability to move to something else, but at this point, it is still all about the applications, and a lot of those require Windows."
A common source of migration failures, says Silver, is whether applications, be they business critical or user specific, will work with Windows 7 or 8.
"In all the migrations that have failed, they have failed because they didn't have a complete list of the applications they needed to run, they didn't test all the applications they need to run, or they have purposely ignored applications which are user or department specific, then realised as they were doing the implementation that those applications were critical, and had to start again," he said.
Walter Cellich, manager of information services at the City of Sydney, said that particular attention was paid to application compatibility in his organisation's migration of around 1,900 XP machines to Windows 7.
The best approach to ensuring compatibility, he says, is to create a comprehensive list of all applications — about 233 desktop applications in the City of Sydney's case — then contact each application's vendor for confirmation on compatibility or the need to upgrade. Where this isn't possible, testing on a trial Windows 7 or 8 machine is recommended. The downside, Cellich says, is that this process can easily be a six-month project.
Loic Herbin, IT manager, APAC, at Campari Australia, says that being late to migrate off XP can have an upside, in that most applications will now be at least Windows 7 compatible or can be upgraded.
"The lucky side of moving so late is that you are pretty sure all the vendors have updated their applications," he said. "But, to be sure, there is a cost, because you will need to upgrade to the next version of the application."
Herbin added that there are also shortcuts that can be taken, such as not cataloguing the applications of every single user.
"We ran a full pilot and targeted one user per department — the most advanced users — and tracked all the software they used," he said. "I think that is pretty standard for any new OS upgrade."
The City of Sydney's Cellich added that one upside of migrating is that it presents a great opportunity to consolidate an organisation's applications for easier management in the future. For the council, that was often as simple as moving from five versions of Adobe Acrobat to one, or three versions of Microsoft Office to one.
"For desktop-specific apps, we chose one variant and decided that was the version everyone would have," he said. "Where we found two apps that did the same thing, we standardised on one."
In having to migrate around 1,900 machines off Windows XP and onto Windows 7, Cellich said the use of the right tools to help automate and accelerate the rollout of both new operating systems and application deployments can be a lifesaver.
The City of Sydney employed Microsoft's System Center Configuration Manager (SCCM) and System Center Operations Manager (SCOM) in particular.
"One thing SCCM does is allow you to pack up your software and then automatically push it out to one or more PCs," he said. "That enabled us to push the SOE [standard operating environment] out, applied it automatically, and then applied the upgrade from XP to Windows 7. It didn't work perfectly, but probably worked on 90 or 95 percent of PCs."
The organisation then used "floor walkers" on the day of the migration to manually assist staff with their PCs.
Gartner's Silver says that there are a multitude of available tools to assist in migrations — everything from inventory or utilisation tools to application testing and remediation, to deployment and automation — but often, finding the correct tool for your organisation and then setting it all up can be a six-month project itself. In that case, it's best to source outside help for your migration.
"If you are just starting to build skills and pick tools now, then you will not be done by April," he said.
"Leveraging a service provider, including using them to improve the overall manageability and for skills transfer for your employees and staff, might be a way for some organisations to get this done and retain some knowledge and get some longer-lasting benefits. Also consider that at this point, even service providers might be stretched by demand."
After so many years on Windows XP, moving your staff to Windows 7 may come as quite an organisational shock. That's why another crucial component of successful migrations is change management.
The City of Sydney's Cellich said he made extensive use of Microsoft educational videos in particular — on topics as simple as how application menus change between different versions of Windows. The videos were available to the organisation for three months before and after the migration.
"Apart from the training videos, we made a virtual machine sandpit area, where people could go and play with Windows 7, see what it looked like, and try our standard apps in that environment," he said. "That was about making sure the business knew what was coming, what it looked like on day one."
Campari's Herbin said that change management was also a factor in his organisation's successful Windows 7 and 8 migrations. Beginning at the top, Herbin ensured that management knew all about the new operating system, and were also some of the first users to have their machines migrated.
"For Windows 8, we trained a super user on the interface — it was considered the biggest challenge — and they in turn trained the rest of the staff," he said. "The approach we took was training one super user per state, and those super users received specific training from Microsoft."
Gartner's Silver advises that a good approach to change management is to create some form of a "Windows migration competency centre", where users and departments can test their tools, get some help in remediating them, and get some kind of virtual or physical sign-off for them.
"There is some communication required to the business that says, 'Hey, we are doing this migration and your department is responsible for testing this application or that application and having it signed off', and that is the only way," he advised.
With just four months to go until end-of-life support, many organisations will have to face the fact that they will still be running some Windows XP machines by April. For Michael Barnes, vice president and research director at research firm Forrester, these organisations need to understand that if they choose to or by necessity remain on XP after April 8, 2014, they do so "at their own risk".
"For instance, as with Windows 98 and Windows 2000, drivers for new hardware will quickly become non-existent, creating compatibility issues," he said. "As with security, third-party solutions will arise to get around these driver issues, but they are not always 100 percent guaranteed for all scenarios.
"Most third-party software vendors will no longer test their software against Windows XP. Hence, there are no guarantees that newer versions will continue to work with Windows XP."
Agreeing, Gartner's Silver says that remaining on XP will introduce risk into organisations. But this can be managed — to an extent.
"Make sure a Windows XP user can't do email; use a Windows 7 machine instead," he advised. "Most security attacks will come through email or the browser, so if the machine can't access the internet or open email, the machine will be that much safer.
"If they have to browse, then you should restrict the use of Internet Explorer 6, 7, and 8 and use a browser that is supported. Also, lock down the PC by restricting administrator access on that device and put an end to any unwanted changes. You can have the PC reboot with a pristine image getting rid of the changes the user has made.
"All of this take time and money, though."