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Take a stroll down the Windows 10 upgrade paths

IT can get lost in a Windows 10 upgrade. Save time and money by knowing the do's and don'ts of migrating to the new OS, and avoid common mistakes.

Change is hard. Change is exciting. Change is inevitable. When it comes to Windows OSes, Windows 10 is the latest change for IT to deal with.

IT administrators can stay ahead of the game by following the right Windows 10 upgrade paths, learning the benefits of Windows 10 and laying out expectations for the migration process. If IT can avoid common problems, understand how to migrate from previous versions of Windows and unleash the potential in Windows 10, it may convince the entire organization that it's time to say goodbye to Windows XP, 7 or 8.

Why migrate to Windows 10?

Windows 10 offers organizations easier management abilities, better support accessibility and a more positive user experience. Windows 10 has enhanced Active Directory features, such as mobile device management integration; greater Microsoft Intune abilities, such as configuring and managing OS update rings; and more advanced Group Policy Objects to help IT lock down endpoints. It can also help IT enforce stricter security policies, such as biometric authentication with Windows Hello. Most users adapt to Windows 10 with little to no training, as many of the controls are intuitive and similar to previous versions. The faster processing speeds appeal to users and can increase productivity.

As part of its complimentary support, Microsoft sends updates and patches for Windows 10. Windows 7 is more vulnerable to attacks because it is has more weak spots, and the Microsoft army now protects Windows 10. Organizations must start thinking about how to wean off of Windows 7, as extended support is scheduled to end on January 14, 2020.

How to migrate from a former Windows OS

There are plenty of organizations that still run older versions of Windows, such as XP, 7 and 8. Windows XP is out of date for the latest hardware, Windows 7 is running on borrowed time and Windows 8 is not widely adopted in the enterprise. Each older OS has different Windows 10 upgrade paths, so it is important for IT to know where to step before migrating.

Windows XP: When migrating from Windows XP to 10, a clean install is best. IT should take an inventory of all the applications users work with in Windows XP and test them with Windows 10. IT will need to update most applications, as well as replace a few due to licensing or compatibility issues. IT will also most likely have to replace some hardware, processors or graphics cards prior to the upgrade to meet Windows 10's requirements.

Windows 7: The upgrade process from Windows 7 to Windows 10 is the smoothest. IT should first check on the licensing costs to make sure it is prepared for the right edition of Windows 10. IT must make sure that all the patches for Windows 7 are up to date so as not to lose any critical security settings or applications. Windows Update runs the migration if IT downloads the Get Windows 10 app, which is also available in Windows 8.1.

Otherwise, IT can use an image file to upgrade to Windows 10. Although many applications from Windows 7 run on Windows 10, it is important that IT double-check this and the hardware requirements prior to the upgrade to ensure an easy transition.

Windows 8: The transition from Windows 8 to Windows 10 is less drastic than XP but a bit more complex than Windows 7. So, IT must proceed with caution in some of the same areas. IT must be running Windows 8.1 with all its updates. An in-place upgrade from Windows 8 to 10 could damage applications. IT has to inventory the applications to make sure they all make it through the migration process. An in-place upgrade should leave most apps and settings in place.

IT admins who are unsure of the readiness level of their old OS can use Microsoft's Assessment and Planning Toolkit. The free utility shows which applications users are working with and how those apps transition into Windows 10.

What are potential Windows 10 upgrade problems?

Just like any road trip, the Windows 10 upgrade paths have hazards.

Just like any road trip, the Windows 10 upgrade paths have hazards. IT admins must look into licensing costs because Microsoft has different pricing per Windows 10 edition. Organizations that use a legacy virtual private network (VPN) client or a device driver from an earlier version of Windows may have problems with Wi-Fi connectivity. Microsoft created an automatic troubleshooting utility to repair Wi-Fi issues when a VPN client is to blame. If an old driver is at fault, IT admins can use Windows Device Manager to determine the compatibility of the driver.

Some companies experienced driver compatibility issues after the first update to the OS, which required more hardware testing. Other businesses struggled with damage to Microsoft Office applications after upgrading to Windows 10. There are several ways to troubleshoot Office issues, but IT admins can try a quick fix by disabling Protected View -- a setting that sandboxes Office processes from other applications to defend against potential exploits.

Organizations should also consider reorganizing the management structure. Windows 10 admins now have the ability to secure the OS from mobile devices, and the OS supports new Group Policy settings. This can cut out extra hands in management but also requires IT admins to oversee more users. Organizations have to make sure users, devices and updates don't slip through the cracks. IT should also keep Windows 10 up to date for patches and updates once the upgrade is complete.

Next Steps

Discover which Windows 10 update branch is the best fit

Find automation tools to make the Windows 10 upgrade easier

How profile and app compatibility will smooth the Windows 10 transition

This was last published in November 2017

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