Migrating to Windows 10: It’s all about the preparation

On 1 August 2015 Microsoft released Windows 10 to enterprise customers. For many IT professionals in your organisation, this will not be the first time they’ve seen Windows 10 as some five million people participated in the Insider Preview beta period, helping to shape the operating system we see today.

For an enterprise, the key to a successful Windows 10 migration is less about the actual deployment and more in planning and preparation for migration. If everything is thought out ahead of time, you can expect an issue free migration for both you as an IT professional and for your users.

Ensure applications will migrate smoothly

Applications enable everyone to do their job so ensuring these will continue to work in Windows 10 is critical. Many applications determine the operating system that they can run on from its internal version number. Unlike Windows 7, Windows 8 and Windows 8.1, which continued the 6.x version numbering to maintain legacy application compatibility, Windows 10 brings a new internal version number of 10.x, so you need to make sure that any applications you use can be installed and function on the new system.

If you have Software Assurance for your Windows operating system licenses, you are entitled to Application Virtualisation (App-V), part of Microsoft Desktop Optimisation Pack (MDOP). This allows you to virtualise your applications into packages and deliver them to users via the network. It can make light work of distributing your applications to the new operating system and can also work around some issues with applications designed for older operating systems. For applications that will not play nicely with Windows 10 or with App-V, you could consider RemoteApp on-premise with Windows Server 2012 R2 or Azure RemoteApp.

Windows 10 still includes Internet Explorer but also has a new web browser called Microsoft Edge which offers a better all-round experience. This means you need to test any web-based applications to check that they work correctly in Microsoft Edge. The alternative is either to direct users to use Internet Explorer for specific applications or to set it as the default browser. You could also use the move as an opportunity to embrace a more bring-your-own-device (BYOD) oriented culture and cross-test your web applications on Firefox and Chrome to allow users to choose the browser they prefer.

Use new features to improve the user experience

Every user will have data and settings that make how they work unique. There are many strategies for handling them, such as the complementary technologies of Roaming Profiles and Folder Redirection, which allow you to store each user’s data and settings centrally. Windows 8 and Windows 8.1 also introduced a new paradigm in the form of Modern User Interface applications from the Windows Store and Microsoft provided User Experience Virtualisation (UE-V), also from MDOP, to help deal with roaming settings generated within these store applications and handle traditional applications in a very lightweight and manageable manner.

If you are using one or more of these methods for centralising your users’ data and settings, have you considered how your core infrastructure could improve the user experience? Windows Server 2012 introduced new features in Active Directory and Group Policy which allow us to define a user’s primary device (or devices) and to only download their roaming profiles and redirected folders on those devices. This eliminates the half hour log-on times some people experience when trying to log on quickly to a hot desk or temporary computer.

If you are not using one of these technologies, perhaps it is time to consider the impact on your users or the business if a laptop was lost, stolen or became irreparably damaged. You may be using Office 365 and OneDrive for Business to store user data in the cloud so it is readily accessible to users working from any location, but what about the settings for their applications?

Microsoft’s User State Migration Toolkit (USMT), used in conjunction with System Center Configuration Manager, can help by identifying the location of user data and settings on a computer and staging them to a State Migration Point while the machine is re-configured for the new Windows 10 operating system. Once the upgrade is complete, the files are copied back to the computer, giving the user a seamless experience and restoring their files and settings back to their original locations.

No need for new hardware

The good news is that Windows 10 does not require any new hardware, so you can migrate the devices you are using today to run Windows 7, Windows 8 or Windows 8.1. One new feature, Windows Hello (designed to replace the password by signing users in with facial recognition) requires a Windows Hello compatible camera which can only be found on the latest laptops, but this feature is unlikely to be required by most organisations.

As with previous versions of Windows, other features such as BitLocker Drive Encryption require specific hardware in the form of a TPM module, but again this depends on whether you want to use this feature. If you have previously relied on third-party drive encryption software such as TruCrypt, news articles about its vulnerabilities in recent months may encourage you to move to BitLocker.

Benefit from a consistent user experience across all devices

Windows 10 introduces a new user experience known as Continuum. This allows the user interface to switch between a tablet, touch friendly interface and a keyboard and mouse friendly interface according to the available hardware, making Windows 10 essential for anyone using a convertible, tablet or touch-enabled notebook. Devices such as the Microsoft Surface or HP Spectre x360 will benefit from this Continuum interface.

Shortcomings in the user interface in Windows 8 and Windows 8.1 for desktop users mean that many organisations have a split environment, with desktop and laptop users running Windows 7 while tablet or convertible users run Windows 8 or Windows 8.1. Windows 10 resolves this gap and allows you to run a single operating system across all device hardware while giving each user the optimal interface for their current device.

Minimise user impact by migrating to Office 2016 with Windows 10

This year Microsoft has also made the next version of Office, Office 2016, available to customers. It should be viewed as a minor update for anyone who using Office 2013 but will be a major update for anyone still on an earlier version of Office. With all the time and effort that goes into planning an operating system version shift, it is logical to make other changes at the same time to minimise the impact over time on your users.

So if you are moving to Windows 10, now could be an ideal time to upgrade from a previous version of Office or begin looking into Office 365. You can then have a rest for a few months until Windows Server 2016 and System Center 2016 are released and you want to start thinking about updating servers!

Use tools to automate the transition

Once you have addressed software applications, web applications, user data and settings planning and testing comes the actual migration. Moving to Windows 10 from any prior version of Windows 10 will be dependent on the size and make-up of your organisation.

For SMEs with a limited number of devices, you may be happy to perform an in-place upgrade of the operating system. The users’ applications, files and settings will remain intact but be sure to have a good backup to hand in case something goes wrong. For medium and large enterprises, performing each upgrade in place manually will be out of the question but there are products from Microsoft which can make the transition easy.

Windows Deployment Services is a Windows Server role which can be configured to install an operating system on a PC over the network and offers little to no configuration beyond installing the operating system. Microsoft Deployment Toolkit is a freely available product which allows the creation of (potentially) complex task sequences to deploy and configure PCs with a new operating system.

System Center Configuration Manager provides all of the above as well as allowing you manage your PC endpoints on a continuing basis, including features such as application lifecycle management, patch management, anti-virus protection, asset management as well as mobile device management for non-Windows devices.

Richard Green, Consultant at Fordway

Image source: Shutterstock/tanuha2001