Windows 10 - When should we upgrade?

Windows 10 - When should we upgrade?

January 20, 2016

There is a lot of buzz surrounding Windows 10 and the “Free” upgrade that Microsoft has made available for a limited time. We are hearing mostly very positive feedback, but there are a few key variables that can cause frustration if not handled correctly and heading into 2016, we want to have a chance to connect with you on Windows 10. We discussing some of the following:

  • How the “free” upgrade has hidden costs – be prepared
  • Typical issues that arise when moving to a new Operating System
  • The three steps to help plan YOUR migration to Windows 10
  • General discussion from audience questions too.


Almost everyone has heard about the new features in Windows 10 and the free upgrade offer from Microsoft. What most people don’t know is what impact the free upgrade can have on a business, both in costs and workflow interruptions. 


In a business environment, it is always necessary to ensure a new technology solution (or upgrade) will not hinder the way your employees work. In this case, it is important to select at least one employee, and in some cases one employee from each department, to use Windows 10 for a period of time before rolling it to the entire company. This will allow you to ensure all applications and peripherals will integrate properly and work the same as they have in the past. If the tester runs into any problems using the new operating system, applications may need to be upgraded and/or processes may need to be changed.
Once testing is complete and potential problems have been eliminated, your IT department or IT service provider should be tasked with performing the actual upgrade. While upgrading a home computer yourself might be appropriate, in a business setting end users should defer to IT to perform major changes like upgrading operating systems. In addition, changes need to be made to Active Directory and Group Policies on the server side. Although Windows 10 will look familiar to most users, some training may be necessary to either learn the operating system or the processes that had to be changed due to operating system compatibility.


Microsoft is offering a free upgrade for Windows 7 and 8 users to help speed adoption of the new operating system; however, this might not be the appropriate timeline for all businesses. The free upgrade period will end on July 28, 2016. Microsoft has yet to confirm the cost to upgrade after. Windows 7 does not go out of support until 2020, so upgrading immediately is not completely necessary. New computers are also shipped with Windows 10 licenses, even if they are currently running Windows 7. This allows more flexibility on when to upgrade, whether it’s upgrading current machines or cycling out old machines according to your lifecycle plan.


Microsoft collects a considerable amount of data with Windows 10 that they haven’t in the past to enhance the user experience. Businesses need to take this into consideration when choosing to upgrade – and in some cases find out if settings can be configured to not share certain information.
Patching updates are configured to automatically push updates to users. This setting can be changed; however, in most cases, patching processes will need to change to reflect the capabilities of Windows 10.

The default browsers for Windows 10 are Edge (Microsoft’s new browser) and Internet Explorer 11 (IE 11). This could cause issues with applications that use a web backend that is not compatible with IE 11. This comes with a huge asterisk, as there are ways to make IE 11 backward compatible, but this will require additional configuration and testing.

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