IT Freedom Blog

A Successful Migration to Windows 10

by Matt Miller on

We recently held a webinar to help our clients understand the particulars of upgrading their companies to Microsoft’s newest OS, Windows 10. Headed by our Chief Development Officer, Matt Miller, and our Chief Technical Officer, Brian Camp, the webinar offered detailed information on Microsoft’s support policies, upgrade processes, and features of the new operating system.




Microsoft Support Lifecycles

To better explain how Microsoft Windows 10 fits in with other Windows versions, Brian Camp began with information about Microsoft product lifecycles, which provides guidelines for product support availability throughout that product’s life.

  • Date of General Availability - when the software is made available to the public.
  • Mainstream Support Phase - during Mainstream Support, the system receives security updates, reliability updates, and the occasional bundled feature pack. This pack provides new features deemed necessary by Microsoft.
  • The Extended Support - in this phase the product receives security and reliability updates only.
  • End-of-Life – at this point Microsoft stops providing security and reliability updates, making the product dangerous to use.

At some point during these phases, the product will reach an End-of-Sale point, when Microsoft has decided to no longer keep the product up for sale, based on the popularity of the product.

Windows 7, 8 and 10 are currently supported. But Windows 7, while still being the most widely used, will reach end of life in January 2020 with Windows 10 being its effective successor.

What Does Windows 10 do Differently?

User Experience

One of the biggest complaints with Windows 8 was the user interface, which removed the Start Menu in favor of a more “tablet-like” interface. Windows 10 addresses these concerns with a return to the familiar desktop interface and start menu. Windows 10 is familiar enough that users with basic Windows experience can easily interact with it.


Cortana is Microsoft’s new search assistant, similar to Siri on Apple products, She can perform searched and respond to a set of verbal commands.

We wrote an in depth blog on the new aspects of Cortana here. (link to Cortana blog)

Microsoft Edge

This entirely new, built from the ground up browser is Microsoft’s answer to Google Chrome. It features modern security and web standards, is compatible with most modern web content and eliminates older technologies that presented security risks in Internet explorer.

Application Compatibility

Whether or not your old apps will work with a new OS is always one of the biggest questions before an upgrade. Windows 10 is generally much more compatible with applications running on Windows 7 compared to the last big jump from Windows XP to 7. Most applications will work properly, however problems can occur with applications that use proprietary drivers (think niche devices like medical scanners) and applications that check for specific OS version numbers. The fact is, that any upgrade requires case-by-case attention, but so far Windows 10 is performing admirably.

*Note: All applications provided to clients by IT Freedom are fully compatible with Windows 10


Microsoft traditionally charges users to upgrade their current operating system, but they have made the Windows 10 upgrade totally free until July 2016. They are being extremely aggressive with their marketing of the offer, using repetitive pop-ups and automated Windows updates to remind users about the free upgrade option.

Though it is free, ultimately there’s no pressing reason to upgrade from 7 to 10 right now. For businesses in particular, upgrading as a part of hardware refresh cycles and/or just for users that have a legitimate need for Windows 10 (developers, IT staff) is a better approach than unplanned upgrades. Though the upgrade path to 10 is relatively easy compared to past versions, upgrading can still be a very disruptive process and could present compatibility problems for your business’ specific applications.

There’s a good chance your older PC will need to be replaced before Windows 7 reaches End of Life anyway, which offers an opportunity to upgrade to 10 as a part of planned hardware refresh cycles.

New PCs

On the other hand, we highly recommend that you install Windows 10 on any new PC. A new PC will almost definitely outlive Windows 7’s extended support period, and any new apps will drop support for Windows 7 shortly thereafter.

*Note: IT Freedom now buys new client PCs with Windows 10 by default

Based on the Windows 10 release so far, we are confident that it will replace Windows 7 in the long term as the preferred Microsoft operating system for business use. Barring specific reasons to avoid it, we endorse buying new PCs with Windows 10 and phasing the new version into business environments.

*UPDATE: Check out our Windows 10 1-Year Later review!

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