Although it will be some time before Windows 10 becomes generally available, it’s never too early to start thinking about the process for upgrading from the current Windows platform. The smart money is currently on a September or October 2015 public release, so savvy system admins can start looking ahead to some inevitable upgrade tools and techniques, along with a few extra tips to help ease the process along.
The Windows Upgrade Assistant
Along with new Windows releases, Microsoft usually makes pre-install evaluation tools available to help users anticipate and prepare for the upgrade process. For the past couple of releases, this has involved a downloadable tool called Upgrade Assistant (here’s a link to the FAQ page for the Windows 8 and 8.1 versions of that tool, by way of example).
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In addition to providing a tool that typically works for recent versions of Windows -- for Windows 10, that will probably mean Windows 7 SP1, Windows 8 and Windows 8.1 Update 1 -- this page also provides useful information about which platforms the tool will support as valid upgrade sources, including required Service Packs that must be installed for the tools to work correctly.
Running the tool usually produces a compatibility report that either indicates that the upgrade can proceed or describes what kind of remediation is necessary to result in a successful upgrade. The items that can appear in such reports generally focus on hardware and software.
For hardware, there may be some devices in use on the source system that will no longer be supported in the target OS, and a warning will be issued to that effect. In some cases, devices may need to be uninstalled prior to upgrade, so that new drivers can be installed for those devices during the upgrade process. In other cases, it may be necessary to hunt down those new drivers after the upgrade is complete. The compatibility report from Upgrade Assistant usually provides information about all such cases.
That said, the occasional unknown device will pop up after an upgrade that will require its identification so that the proper driver can be located and installed, if such a drive is available. Several good tools to help resolve the appearance of unknown devices in Device Manager are available, including Unknown Device Identifier and the SourceForge project UnknownDevices.
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For software, certain programs may in some cases be identified as no longer supported under the new target OS. In other cases, it may be necessary to update to a newer version of a program currently in use. In still other cases, it may be necessary to uninstall a program prior to an upgrade, then reinstall the program following the upgrade.
Admins will want to carefully consider building new reference images for widely used systems instead, especially if they already plan to use automated deployment tools to drive their upgrade process along. To that end, eligible parties may want to compare the capabilities that a Software Assurance license from Microsoft will convey via its Microsoft Desktop Optimization Pack (particularly if used in tandem with System Center), or the Microsoft Deployment Toolkit versus any number of excellent third-party products from vendors such as SmartDeploy and PDQ Deploy.
The Big Problem With Software Upgrade/Migration
Applications can serve as an elephant in the room when it comes to Windows upgrades. This is because there will be occasions where mission-critical or line-of-business applications can’t make the move from current standard Windows platforms to some newer target OS version. In these situations, a remedy must be researched and worked out before migration can proceed, or else some or all users will find themselves suddenly unable to do their jobs.