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How to Upgrade Windows Servers 2008 and 2008 R2 Before Their Support Ends

Microsoft recently announced their end of support for Windows Servers 2008 and 2008 R2 coming up next year on January 14, 2020. What does this mean for businesses that are still running on these servers? Well, after the end of support date, any computer still operating on these systems will be especially vulnerable to viruses and hacks to its system, due to the regular security updates that will end alongside Microsoft’s technical support for those servers.

Luckily, your business has plenty of time to upgrade your 2008 and 2008 R2 servers before the end of support date. Tie National has laid out a simple guide for your to follow for these separate Windows Servers. Let’s dive right in!

Upgrading Windows Server 2008 to Azure


  • Take stock of your current files and applications.


Before you start upgrading your server, it’s a good idea to look at your current programs and databases and see which will benefit your company the most: migrating to the Azure cloud or manual, on-site upgrading? Rank your programs and databases according to their current impact to your business, and develop an upgrading timeline that is based on how long each individual item will take.


  • Move/backup your files and databases to a secure site/drive.


To ensure that no crucial information is lost as a result of a crash, backup all of your files and applications onto an external hard drive and/or move what you can to the Azure cloud server. Your assessment in Step 1 will determine where either all or most of these items end up.


  • Upgrade your system.


Finally, the moment we’ve all been waiting for! Microsoft has a wonderful guide that you can follow that outlines each individual path you can take when it comes to choosing the right upgrade path for your business. If you’ve decided to upgrade your Windows Server 2008 the old fashioned way (on-site), simply make the upgrade from Windows Server 2008 to Windows Server 2016 (or 2019, depending on your preference).


  • Secure, Optimize, and Maintain your new and improved servers.


After your systems have completed their upgrade/migration, you can either use your computer’s built-in security program or a local IT specialist to run diagnostics and make sure that the upgrade was successful and that your servers are running correctly.

After all that hard work, it would be terrible if your new servers crashed. Tie National provides on-going technical support, no matter the release-year of your Windows Server. Our IT specialists can assist you with the upgrading process, as well as perform on-going maintenance to ensure that your business continues to run smoothly. Call now to learn more! 630-301-7444

How to upgrade your Windows Server 2008 R2 to Windows Server 2019


  • Repeat Step 1 and Step 2 from the Windows Server 2008 upgrade guide.


Make sure that any important files, databases, and programs are backed up accordingly.


  • Shut down and close out of all applications.


In order for a successful upgrade, any Virtual Machines cannot be running or open. This includes Shutdown, Quick Migrate, and Live Migrate.


  • Start the upgrade path.


Upgrading Windows Server 2008 R2 is a little trickier, but don’t let that deter you. An IT support specialist can assist you with any issues you might have during the process.

The server upgrade path will go as follows:

Windows Server 2008 R2 > Windows Server 2012 > Windows Server 2016 > Windows Server 2019

Make sure that you upgrade to each individual server in the order listed above. A direct upgrade from Windows Server 2008 R2 to Windows Server 2019 could cause a system crash or worse, a loss of your important files and applications.


  • Secure, Optimize, and Maintain your new and improved servers.


Again, make sure that your new systems are running smoothly to ensure that all the time you spent upgrading doesn’t turn out to be fruitless.

A newer system for your business means a faster, productive, and more organized workspace. If you’re having trouble upgrading your servers and Microsoft’s end of support date is fast approaching, consider getting assistance from a professional. Tie National is comprised of a team of experienced IT professionals across the nation that can help your business’ upgrade go smoothly. Learn more about Miami IT support, Atlanta managed IT services and Houston IT Support.  Call today to schedule a service! 630-301-7444


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