Windows Server 2008 End of Life: Should you Upgrade to Azure or Windows Server 2019?

If your servers are still running Windows Server 2008, you have less than six months to move to a new, supported, generation of Windows Server such as Windows Server 2019. Don’t ignore this end of support deadline, or the loss of OS and application support could have an extremely disruptive impact on your organization.

Windows Server 2008 End of Life


Why is this End of Support deadline such a big deal? There are a few different reasons…

3rd party app vendors cannot fix bugs if the underlying operating system is no longer supported, so once Microsoft ends support for Windows Server 2008, most ISVs will also drop support. And that is a big problem, but not the only concern…

These outdated systems are extremely vulnerable to cyber-attack. Cybercrime is getting more and more advanced, and these systems simply were not designed to keep up. Come January 2020, free security updates will be terminated, leaving your IT susceptible to all sorts of cyber security issues.

You may have heard that Microsoft will provide extended security updates for those who migrate Windows Server 2008 to run on Azure Virtual Machines (VMs)… so, why doesn’t everyone just do that?

There are a few things to note about this:

1) Azure will provide security updates, but the OS itself will still be unsupported and most of the applications running on those VMs will not be supported…  not ideal!

2) The experience of running VMs on the cloud is VERY different from what most users expect from a true cloud experience… For example, with VMs, if you undersize the system requirements for an application, or if your compute requirements increase, the VM does not scale automatically. You have to manually reconfigure the system and reboot. The same goes if you over-provision the VMs and your monthly spend is higher than it needs to be… This means these VMs must be constantly monitored, and then manually reconfigured and rebooted to scale up or down.

3) MANY of the features that Azure customers take for granted (availability, redundancy, and backup for example) have to be configured manually with VMs.

So, what is the alternative?

Windows Server 2008 to Windows Server 2019 Upgrade

For applications that do belong in the cloud, Azure PaaS (Platform-as-a-Service) provides a number of key benefits compared to VMs: automatic scale up and down to meet demand or reduce costs, built in load balancing & traffic manager for high availability and performance, increased security, and less management required on the user’s part.

For applications that can be run more efficiently, or more economically, on-prem,
Windows Server 2019 on HPE ProLiant Gen10 Servers provides back-end support, and access, to Azure, so applications aren’t lost during outages, users can protect and restore data, both Azure and on-prem servers can be managed from a single, integrated view, and advanced

And, for Azure applications that are best run on-prem because of cost, or regulatory compliance, or performance, HPE ProLiant for Microsoft Azure Stack is an ideal complement to the Public Cloud.



Windows Server 2008 End of LifeWindows Server 2008 End of LifeNew features in Windows Server 2019 make it easy to manage both on-prem 

applications, along with Public and Private cloud deployments, and this hybrid solutions is a much better solution long term, compared to moving old, unsupported apps to run on VMs in the public cloud.

The cloud is a journey, it’s not like flicking a light switch… and the journey begins with a modern version of Windows Server.


Kyle Todd.jpg

Meet our guest blogger: Kyle Todd

Kyle Todd is the Hewlett Packard Enterprise Category Leader for Hybrid IT. His focus is Microsoft-based solutions. He has held a variety of roles at Hewlett Packard Enterprise/Hewlett Packard including Channel Management for Mission Critical Solutions and SAP HANA.


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