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Should You Migrate Windows 2008 to Windows 2019 or Azure?

Pete Young | | October 17, 2019

A flock of migrating birds.

As you probably know, Microsoft will no longer support Windows Server 2008 as of January 14, 2020. Your challenge is to determine how to migrate your servers to a new platform. If you stay with Windows Server 2008, you’ll expose your company to a variety of risks that could cause problems you don’t want to cope with.

Learning as much as you can about your migration alternatives will make the decision easier and set the stage for a successful migration.

What Happens If You Don’t Migrate?

Every time Microsoft stops supporting one of their products, there are always people who think that staying with the status quo is the best option. Unfortunately, there are many risks of running unsupported Windows 2008.

Avoiding cyberattacks is difficult enough when you have full support for all of your systems. Without security patches, your systems are going to be vulnerable. If you don’t migrate, you’re betting your business that you won’t get hacked.

Your systems will become unreliable, slowing down critical operations and increasing maintenance costs. You could also run into problems with compliance and getting third party software to operate efficiently.

The worst problem is that you could end up losing your competitive edge as others in your industry take advantage of new software that will only run on upgraded systems. Migrating your systems is the only solution that will ensure your company’s profitability in the long run.

What Happens if You Use Microsoft’s Extended Security Update Program?

According to Microsoft, they don’t offer the Extended Security Update (ESU) program as an alternative to migrating to the latest operating systems. It’s only available as a last resort if customers find themselves running a system after the end of support date.

The best approach is to plan to complete your system migration before Windows Server 2008 support ends. If that’s not possible, you can use the ESU program to support the completion of your migration with minimal security risk.

The ESU only includes critical security updates. Therefore, the operating system itself will remain unsupported. The program doesn’t include any technical support to address the security vulnerabilities, although you may be able to get support based on some other Software Assurance coverage you hold. In addition, you won’t have access to new features, customer-requested hotfixes on topics other than security, or design change requests.

For on-site systems, you will need Software Assurance or an equivalent Server Subscription in order to buy ESU coverage. For Azure systems, participation in the ESU program is automatic at no charge, but you’ll need Software Assurance or Server Subscription to use the Azure Hybrid Benefit.

Choosing Between Windows 2019 and Azure

If you’ve decided to take advantage of cloud processing for all of your operations, now is an excellent time to make a move to Azure. Microsoft builds security and privacy into the Azure platform, and it supports Windows applications and services along with open source technologies.

Other features include over 90 compliance offerings and services and products targeted at a variety of industries that can help you streamline your operations to the greatest extent possible. It also allows you to manage a hybrid infrastructure easily. In fact, 95 percent of the Fortune 500 companies use Azure.

Microsoft is offering incentives to make your decision even easier. You can reduce costs with Microsoft’s free extended security updates when you “migrate your Windows Server and SQL Server 2008 and 2008 R2 workloads to Azure virtual machines.”

Windows Server 2019 is an excellent solution when you need a hybrid environment. This operating system provides excellent hybrid support when you use it with Azure. The Windows Admin Center is browser-based, allowing you to manage workloads that are running on-premise and in Azure all in one place.

Windows Server 2019 doesn’t require that you develop a custom solution for hybrid operations. You can use the skills and knowledge already available among your staff to expand your data center into the cloud. You’ll also be able to take advantage of the additional layers of security that are available when you use Windows Server 2019 and Azure together.

A Good Migration Plan is Critical

You’ll be able to take advantage of all the benefits of the new Windows Server technology when you develop a migration plan that ensures a smooth transition. Learn more about responding to end of support issues and best practices for developing your migration plan by downloading our latest whitepaper, “It’s the End of Life for Windows Server 2008.”

If you’re looking for a migration partner, Datavail is a Microsoft Gold Partner with the expertise and resources you need to make a smooth transition. Call us at 866-811-6676, or send an email if you’re ready to get started.


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