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When IT performs an operating system upgrade or migration, the best practice has traditionally been to automate the process.
Turning to automation makes sense because manual upgrades and migrations do not scale well. It's one thing for IT to perform a manual upgrade to Windows 10 on half a dozen desktops, but it is quite another thing to do it on 1,000 desktops. Furthermore, automation can nearly eliminate the potential for human error.
Even so, there are some instances where a manual upgrade is actually the way to go.
Why manually upgrade to Windows 10?
There are several reasons why a manual upgrade to Windows 10 could be the best course of action. For example, if IT only needs to upgrade a small number of desktops, it may actually be faster and more efficient to perform the operation manually than to take the time to automate the process.
Another reason why IT should perform a manual upgrade to Windows 10 is that data exists on the desktop IT wants to upgrade. This won't be too much of an issue in many cases because the vast majority of organizations require users to save data to a network share or to cloud storage so the data is backed up.
Users who work for really small companies or users who are full-time road warriors often save files and other data directly to their desktops' hard drives, however. An automated migration would likely destroy this data, especially if IT is also reimaging the desktop's hard disk as part of the migration.
On a similar note, IT pros may opt for a manual upgrade to Windows 10 if they no longer have access to the installation media for the older software the desktop runs. This can happen if the desktop runs an older application and IT has misplaced the installation media or if the installation media is damaged.
Likewise, IT may need to manually upgrade a desktop to Windows 10 if that desktop runs an abnormal configuration. For example, if a desktop runs a dual-boot configuration where it can run more than one OS, then IT pros probably would not want to perform an automated migration to Windows 10. Doing so would likely eliminate the desktop's ability to boot to the alternate operating system.
Likewise, IT may need to perform a manual upgrade to Windows 10 if the desktop uses a storage controller that Windows 10 is unlikely to natively recognize.
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