Windows 7 and Windows Server 2008 – Less than one year to upgrade

Your New Year’s resolutions have been set (and maybe already broken). But one thing we think you should make sure is on the list is the plan to upgrade your Microsoft infrastructure.

As you may already know from the Microsoft announcement, support for Windows 7 and Windows Server 2008 and 2008 R2 will end on January 14, 2020 – less than one quick year from now.


Reasons to Upgrade

After January 14, 2020, these operating systems will no longer receive security updates from Microsoft. This is important because attackers are constantly finding new ways to exploit these operating systems. Today, when a new vulnerability is found, Microsoft fixes it with a security update. The attackers will continue to look for ways to exploit these operating systems so if you are using them after January 14, 2020, you are taking a huge risk.

Other important reasons to upgrade:

  • It is important to stay current for compatibility reasons. Other line of business applications that need to run on the servers typically require a current operating system.
  • Support of your servers and workstations by Managed Service Providers like NG2 is limited if the systems have been marked end of life.


Upgrade Options

For Windows 7, the suggested upgrade path is to Windows 10 which provides improved design, performance and security.

For Windows Server 2008, there are two upgrade options depending on your needs and IT resources:

  • Windows Server 2016/2019 – Upgrading to these versions are important for security, compatibility, and support reasons. The newest releases also add new features which provides administrators with robust management tools that deliver powerful automation and integration capabilities, plus an easy-to-use GUI.
  • Windows Server Azure cloud infrastructure – This option provides a flexible approach to move to a cloud-based model and potentially save you money. You will also benefit from the new capabilities of the latest Windows Server infrastructures to improve your security and reliability.


We strongly suggest to get started on the planning in Q1 2019. The key reasons to start now are:

  • To ensure you have the budget allocated during 2019
  • These migrations/upgrades take time to plan and execute
  • You may have Q4 freezes due to holiday or other reasons which may require you to upgrade by Summer 2019


Overall System Refresh Approach

You may want to take this opportunity to review the age of all your IT infrastructure components. NG2’s philosophy is that all business critical servers and network systems should be proactively replaced every 5-7 years. And end-user workstations should be replaced every 3-5 years. After these timeframes, the likelihood of a failure increases significantly, putting your organization at risk of lengthy downtime in the event of a crash.

To help plan and implement your upgrade, Microsoft suggests the approach of assess, migrate, optimize which is a solid approach. The challenge is that you need to do this with your already tight resources that are overbooked. NG2 can help you get started via an assessment, provide recommendations and develop a plan during 2019 – all while minimizing costs and disruption.


To discuss your situation, contact me and we can discuss. We look forward to helping you meet at least one of your New Year’s resolutions.

Dan Grady (here’s my LinkedIn)
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