Microsoft announced the Windows 7 End of Life effective in January 2020. Microsoft will no longer provide free security updates or support for Windows 7 and Windows Server 2008/ 2008 R2 operating systems (OS). This means there is no more patches available and no more technical support from Microsoft’s support center. If you continue using Windows 7 and Windows Server 2008/R2 after that date, your systems are at risk due to potential new vulnerabilities and cyber attacks, unless you plan on paying for Windows Extended Security Updates (ESU).

With ESU support fees starting at $25 per device and doubling each year after 2020, running Windows 7 and Windows Server 2008/R2 in your environment will quickly become very expensive.
To avoid paying these high support costs and to enable successful migration, companies should make the move and upgrade to Windows 10.

What Are the Major Risks?

Risk of Vulnerabilities and Cyberattacks

In 2018, there were 499 Windows desktop OS vulnerabilities reported across Windows Vista, Windows 7, Windows RT, Windows 8/8.1, and Windows 10. Of these, 169 were considered critical vulnerabilities. During the same period, there were 449 Windows Server vulnerabilities, of which 136 were critical. While there was a slight drop in the number of Windows vulnerabilities from 2017 to 2018, over the past 6 years the number has nearly doubled.

The infamous WannaCry ransomware attack, which infected over 200,000 computers worldwide in May 2017, was the result of an unpatched vulnerability that affected Windows OS. Microsoft had released patches for the vulnerability in March 2017, but only for the operating systems it currently supported (Windows Vista and above). It was estimated that 98% of the infected computers were running Windows 7, one of the supported and patched versions of Windows at that time. If a WannaCry type of cyber attack occurs after January 14, 2020, and it affects Windows 7, you’ll only get a patch if you are paying for extended support.

The High Cost of a Data Breach

One in three breaches caused globally is due to unpatched vulnerabilities. And data breaches can be more devastating to small and medium-sized businesses than floods, fire, and transit strikes combined. Data breaches could very well end your business.

The global average cost of a data breach in 2018 was $3.86 million with the average cost for each lost or stolen record weighing in at $148.3 Imagine the cost your company may incur by not migrating to Windows 10.

Applications Will No Longer Run On Windows 7

Microsoft will no longer support Office 365 ProPlus on Windows 7 for free, which means staying on Windows 7 will again cost you more money. Similarly, many independent software vendors (ISVs) are unlikely to support new versions of applications on Windows 7. For example, Adobe has already announced that its next major Creative Cloud update will no longer support older versions of operating systems, such as Windows 7, 8, and few early versions of Windows 10.4

What’s Holding Businesses Back From Upgrading?

It’s been four years since Windows 10 has been released, but many businesses are yet to migrate to it. As always, OS migration is a major IT transition for any business. According to a survey conducted by Kollective — an enterprise content delivery platform, two-thirds of businesses have not developed a strategy to migrate to Windows 10, and about a fifth of those questioned was not aware of the end of support news.

Also, many businesses simply do not have the IT infrastructure in place to implement mass migration and would probably need years to migrate manually.

Users love Windows 7

Some users say that they love Windows 7 and are reluctant to switch to Windows 10. They do not want to let go of the familiarity. So what can they do about this? Well, for starters, users can configure Windows 10 to look and act more like Windows 7.
Here’s how:

  • Get a Windows 7-like Start Menu with Classic Shell: Install the free program Classic Shell and get your start menu to look similar to Windows 7.
  • Remove the Cortana Box and the Task View Button from the Taskbar: Windows 10 has a search field in the taskbar which invokes the Cortana Box when clicked. You can remove this by right-clicking on the taskbar and going to “Cortana” and select “Hidden”. To disable the task view button deselect “Show Task View Button”.
  • Add Color to the Windows Title Bars: The Windows 10 title bars are white in color by default. To change the color to these head to Settings > Personalization > Colors.

What’s Great About Windows 10?

Moving all of your users and computers from one operating system to another is no small feat. But, Windows 10 has some great enhancements that make the migration worth the effort. A few of the crucial ones are:

Enhanced Security

Windows 10 is more secure than any of Microsoft’s previous desktop OS versions. Major security enhancements include advanced biometrics (hardware dependent), advanced threat protection, malware protection, and trusted hardware. The secure boot feature from Windows 8 received an upgrade in Windows 10 making it more secure. The secure boot requires that any program that begins as the operating system starts, needs to be signed off by both Microsoft and the hardware manufacturer. Windows 10 makes this feature mandatory by not letting users bypass it.

Faster Startup

Speed is the reigning capability of Windows 10 whether it is in the case of system startup or application performance. A speed boost specifically aimed at gamers comes from DirectX 12, the new 3D engine, that gives developers more console-like “closer to the metal” access to graphics processors. It offers much improved overall performance of the system with power savings of up to 50 percent.

Seamless User Experience

Windows 10 has the same core on all devices which makes it familiar and easy to use, no matter what device you use. It also has the popular Start button which was missing on Windows 7.
Another major Windows 10 enhancement is the usable touch screen mode. The touch screen helps users work more quickly and efficiently than with a mouse or touchpad.

What Are Your Options Now?

Staying on Windows 7

Even after Windows 7 end of life your organization absolutely must keep certain machines on Windows 7, then you have a couple of options:

  1. Pay for ESU as discussed above. A costly option.
  2. Windows Virtual Desktop on Azure — If you are already using Azure services — Microsoft 365 or Windows 10 Enterprise, you can run Windows 7 and Windows 10 virtual desktops in the cloud. Windows 7 ESU updates are included for free for three years after the January 2020 end of life date, in this service.

Moving to Windows 10 and Windows Server 2008

Migrating from Windows 7 to Windows 10 is the only real option for businesses in the longer term. And, businesses have a few different ways for moving off the end of life Windows Operating Systems.

  1. Upgrade your hardware and get the new OS automatically
    • Organizations will automatically get the new Windows 10 OS if they buy new PC hardware. Similarly, new servers will, of course, come with a supported version of the Windows Server OS. You can either buy or lease the new machines. Leasing can align with your hardware refresh cycle, which is typically three to five years.
    • New computer hardware, like the newer OS, has better security features. The new hardware may not add much performance, depending on how old your existing hardware is.
  2. Keep your hardware and migrate to a new(er) version of the OS.
    • Migrate from Windows 7 to Windows 10 for desktops and laptops — See our Windows End of Life Checklist.
    • If your Windows 7 hardware is less than three years old, you can simply upgrade to Windows 10. If it is older than that, then you probably would want to purchase new hardware anyway.
    • Microsoft licensing is notoriously complex and Windows 10 licensing is no exception. There are a number of different licensing options for Windows 10. These include:
      • Windows 10 Pro Upgrade License — This license is recommended for customers that want to upgrade Windows 7 Pro machines to Windows 10 Pro.
      • Windows 10 Enterprise E3 Device or User based license
      • Windows 10 Enterprise E5 Device or User based license
      • Microsoft 365 Bundle — This includes a license to Windows 10 Enterprise or Business, Office 365 and Enterprise
        Mobility + Security.
    • See the Microsoft Volume Licensing Guide for Windows 10 to learn more.

Migrate from Windows Server 2008/2008 R2 to Windows Server 2012/2012 R2, 2016 or 2019

Determine the OS version that best fits your business and migrate to one of the following — Windows Server 2012/2012 R2, 2016 or 2019.
Here is a comparison of the various Windows Server versions for your reference.


Windows 7 End of Life is here, and there is nothing users can do about it. There are several reasons why so many small and medium-sized businesses continue to run their computers on Windows 7 and Server 2008 EOL. Aside from familiarity and resistance to change, many are running older software applications that are also past their useful life and therefore won’t run on Windows 10. But there’s a ton of new software and technology now available, and affordable alternatives are generally available for almost any legacy application out there.

Don’t put your business at risk by staying with unsupported Windows OS versions. Even a machine not connected directly to the internet could be infected through file sharing and imports. Let us help you identify which machines are still running Windows 7 and Windows Server 2008. We can also let you know if your current hardware is capable of running Windows 10, recommend alternative software if needed, and guide you on steps to take to upgrade.

Ask us how we can help you migrate your Windows 7 machines!  Please contact us today to get a professional assessment.