All good things must come to an end. If you are currently running Server 2008 or Server 2008 R2, you cannot ignore the reality that Microsoft will terminate extended support for those operating systems, establishing their End of Life (EOL) on January 14, 2020. This date will also include SQL Server 2008 and Windows 7. Yes, it is tough to say goodbye to something good.  Windows Server 2008 was an extremely successful product for Microsoft and served so many organizations well. Estimates from a principle program manager within Microsoft indicate that Server 2008 still makes up nearly 40 percent of active Windows Servers running in the world today. What’s more, almost 500 million applications are still running on some form of Server 2008.

Mainstream and extended support defined

For those unfamiliar with the Microsoft support model, the company offers two support periods; mainstream support and extended support. Mainstream support typically lasts for five years. During this time, Microsoft commits to regular feature updates, design changes, warranty claims, patching and security updates. For Windows Server 2008 and Server 2008 R2, this support level ended on January 13, 2015. Since then, the server OS has been covered by extended support. This is a minimum support level that includes continued patching for bugs as well as security updates. These types of updates are imperative because hackers and cybercriminals continue to discover vulnerabilities within all Windows operating systems. They then use these discoveries to create malware and attack strategies to exploit them. While an OS may grow stale during the extended support period due to the lack of innovation, it remains safe to use. Once extended support expires this coming January, enterprises that continue to operate Server 2008 will become the wild, wild west as exploitable vulnerabilities will no longer be patched.

Why a un-supported OS is so dangerous to your network

Upgrading operating systems is a time consuming task that is often, deferred to another day. If we look back to 2017. the summer of WannCry, to witness the potential cost of postponement. The infamous encryption malware strain shut down enterprises worldwide. This illustrated how a Windows bug can quickly turn into an international incident. In this case, the culprit was the unsupported and forgotten XP operating system.

Since 2017, another exploitive threat has come on the scene called Smominru. Smominru is a botnet that targets Windows machines using a combination of exploit worms and brute-force attacks. Its rapid infection rate has been staggering infecting an average of 4,700 computers a day. Windows 7 and Server 2008 represent 85 percent of all infections. One can presume this rate will multiply once extended support ends.

No good on-premise options

The cost of inaction is expensive. For those who want to retain the option to do nothing, Microsoft is selling extended support for both Server 2008 and SQL Server 2008 (for both the original and R2 versions). It is not cheap. Pricing will be 75 percent of the Enterprise Agreement prices for the latest version on an annual basis. You must pay up front for the first year and you must pay for the full calendar year regardless of enrollment date. You also cannot skip the first year without paying for it.

You can upgrade, but the path to the latest OS is not easy. Server 2008 does not directly upgrade to Server 2016 or Server 2019, first requiring an upgrade to Server 2012 and then a subsequent upgrade. Keep in mind that Server 2012 loses extended support in 2023. Then there is the issue of whether your hosted applications associated with these older versions will be compatible with their newer replacements.

The opportunity

When one door closes, another opens. That is certainly the case with your on-prem Server 2008 or SQL Server 2008 install. Microsoft is incentivizing companies to migrate to Azure by offering an additional three years of free extended support. Microsoft is only offering this for VMs that reside in Azure. For those who have wanted to accelerate or complete their digital transformations, this is a great opportunity.

Migration prerequisites to ensure success

Do you know exactly how large an impact the coming Microsoft Server 2008 EOL will have on your enterprise? Simply knowing the number of installed instances is not enough. You need to know all of the applications, services and resources associated with them as well. Yes, there is some prep work to do but iQuate makes it easy with iQCloud’s automated service mapping capabilities. This enables you to accurately determine the true size of your Server 2008 and SQL Server 2008 footprints regardless of your enterprise architecture. The discovery process automatically maps your business services in a matter of hours so you can fully understand the impact from all Microsoft EOL dependencies. Use the data and insights from iQCloud to accurately plan your migration roadmap and modernization efforts.

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