By now, everyone should be aware that Windows XP is an unsupported, unsafe operating system for business and personal use in 2016. Perhaps lesser known is that Windows 7, XP’s rightful heir in many organizations today, entered end of mainstream support last year. In fact, all support options for Windows 7 from Microsoft have expired except for extended support – offered through January 2020 – which only offers security updates, pay-per-incident system support, and access to Microsoft’s Knowledge Base resources.

With this in mind, many organizations today need to be considering their OS contingency plan. After all, 2020 is not far off.

Those businesses aiming to be proactive with their OS migration may also be interested to know that Microsoft’s free upgrade offer for Windows 10 expires on July 29, 2016.

Now, not every organization will have access to the free offer; Windows 7 and 8/8.1 Professional editions are eligible, but Enterprise versions are not. Whether or not your business is able to take advantage of the free upgrade depends on your particular Windows licensing agreement. As a general rule, if your business purchases your software licenses as you add PCs, you should have the ability to upgrade for free. If, however, your organization practices volume licensing, you will likely not be eligible. Check out Microsoft’s FAQs resource for more information on upgrade qualifications.

Regardless of whether or not you can upgrade for free, Windows 10 is a practical and proven platform for businesses today, particularly for those organizations already operating on the Windows platform.

There are, of course, key considerations when weighing a move to a new operating system – Windows 10 or otherwise. To help, we’ve compiled our list of the priority questions to be asking internally to ensure your environment is prepared for an upgrade.

Key Considerations
  • Will your current hardware meet or exceed the new operating system requirements?

    RESOURCE | Windows 10 Specifications

  • Do your line of business (LOB) applications work on the new OS? Does the vendor for each business-critical application confirm that they will support their application on that operating system?
  • Does your current endpoint protection software – antivirus, et al. – operate on the new system?
  • For Windows 10 upgrades in particular, are there any web based applications you use and do they support Microsoft Edge or Internet Explorer 11? Are there any browser plugins that need to be supported by a newer edition of IE?
  • Do your printers, scanners, or other peripherals have supported driver compatibility on the new OS?
  • Are there new features in Windows 10 that your business would benefit from?
  • Are there features in Windows 7 that you would lose in a move to Windows 10 or another OS? How does that affect your business operations?

A helpful tool for evaluating a potential Windows upgrade or platform migration is the Microsoft Assessment and Planning (MAP) toolkit which collects data on the readiness of your infrastructure environment and provides a report to help determine if there will be any issues to address prior to the system upgrade.

If and when you decide to move forward, we always recommend a test pilot for businesses, upgrading one computer in each department for a trial period. You have 30 days to revert back to Windows 7 if you find a compatibility issue, which is easier scoped with a pilot program rather than an organization-wide mass update.

Additionally, another important consideration when upgrading your operating system is examining your business’ Active Directory environment. A Windows Server 2012 R2 environment will better support Windows 10 with newer features and upgraded Group Policy options. For those businesses running Windows Server 2008 or 2003 – which entered end of life last year – we would recommend upgrading your servers and the related Client Access Licenses (CALs) prior to upgrading or replacing workstations to ensure full support is available.


Staying ahead of the technology lifecycle of your business tools is a wise practice from both a security and sustainability standpoint, because, as we all know, technology today is progressing at unprecedented rates. The businesses that will find success will be the ones that use this to their advantage.



Mike Arvidson is the director of Eide Bailly Technology Consulting’s Infrastructure Services. With more than 20 years of experience in the IT industry, Mike’s wealth of knowledge includes network systems implementation, integrated new technologies, and information security.

Topics: IT Infrastructure & Security