Deadlines have a way of getting your attention.

On January 14th, 2020, Microsoft will stop providing security updates for Windows Server 2008, almost nine years after the last major update to the operating system was released. No company can afford to operate technology infrastructure knowing they’re on their own if new, critical security holes are discovered, and there are a larger number of application workloads running Windows Server 2008 in 2019 than you might think.

In general, CIOs and IT managers at big companies have always been conservative with their application infrastructure, adhering to that old adage that if it’s not broken there’s no need to fix it. But that understandable mindset, given that CIOs only get noticed when their infrastructure breaks, means that a surprisingly large number of companies have put off this decision.

Cloud companies smell money.

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This is a massive opportunity to move a significant chunk of application workloads from self-managed servers to cloud servers, and Amazon Web Services, Microsoft, and Google are all hoping to win big pieces of that business. It’s also a boon for professional services firms like Seattle’s Skytap and Slalom that make their living helping companies move out of data centers and onto cloud services, a process you’ll be able to hear much more about next week in Bellevue during the Cloud Migration track at the GeekWire Cloud Summit.

“This end of support milestone is a great opportunity for a lot of our customers to transform their applications and infrastructure,” said Arpan Shah, general manager for Azure Infrastructure Product Marketing at Microsoft. That opportunity, however, is also setting up a great competition among the cloud vendors this summer to be part of the “digital transformation” they love to trumpet.

Here comes the cloud

Windows Server 2008 was first released to the world in February 2008 by former Microsoft and Snowflake Computing executive Bob Muglia, and what a different world that was. Months ahead of one of the worst financial collapses in modern history, enterprise companies doing business at scale were still managing their own hardware for virtually all of their applications.

Linux had made its mark on enterprise computing at that point, but Microsoft still commanded the lion’s share of server operating system market share, with around 66 percent of the market according to Reuters in 2008. That equation has flipped in the intervening years, but there are an awful lot of web sites and applications designed around Windows Server 2008 that are still in use.

Windows Server 2008 “was one of the most successful product launches in Microsoft history,” said Vikram Ghosh, vice president of business development at Chef, who worked for Microsoft’s Server and Tools division at the time it launched. Today, there are still around 500 million applications running on the operating system that can be detected on the public internet, which means there could be many more inside corporate networks, he said.

Microsoft declined to release its own data on the size of that opportunity, but Sandy Carter, vice president of Windows and enterprise workloads at AWS, estimated that half of the servers running applications on premises are using either Windows Server 2003 (support for which expired in 2015) or Windows Server 2008.

Given that the public cloud only accounted for about one-third of worldwide IT infrastructure spending in 2018, according to IDC, you start to get a sense for how many applications will need to upgrade.

In his experience, the decision about whether or not to upgrade older applications “always came down to time, resources, and priorities,” said Dan Jones, vice president of product at Skytap and another former Microsoft executive with experience in Nordstrom’s IT operation.

And a lot of those customers are also looking at the end-of-support deadline for SQL Server 2008, which arrives in just a few weeks in July. Companies staring down the barrel of these deadlines have a few options, but they need to start moving.

East versus West

As might be expected, Microsoft is hoping to get as many of those customers to stay within the family as possible with incentives that blaze a trail to Microsoft Azure.

Microsoft is offering a free extended security update plan to Windows Server 2008 customers that migrate to Azure, which promises to provide patches for security issues for up to three years if they move to Azure. Microsoft also offers that three-year plan to companies managing their own servers or using other public clouds to run Windows Server 2008 applications, but it will cost you: Carter warmed this New Englander’s heart by describing the lifeline as “wicked expensive,” and Shah said the security updates cost “effectively 75 percent of the cost of a(n operating system) license per year.”

But if you’re happy to move to Azure, Microsoft’s plan gives you time to decide the best upgrade path for your applications. A lot of customers just want to get into Azure under the deadline without changing anything about their Windows Server 2008 apps, and customers who do so will also enjoy having Microsoft apply those security patches for them while they figure out their next move, said Wisam Hirzalla, director, operational databases and blockchain product marketing at Microsoft.

Companies that plan to manage their own servers for an extended period of time have likely already upgraded to newer versions of Windows Server, but companies that are still running Windows Server 2008 have to reconfigure their applications twice — first for Windows Server 2012, then for 2016 or later versions — if they want to upgrade, because there is no direct path to Windows Server 2016 from a server operating system first released when George W. Bush was still president. That’s a great forcing function for companies that have been thinking about making the move to the cloud at some point anyway.

AWS built an upgrade tool for Windows Server 2008 users to take that first step to Windows Server 2012 while running their Windows Server 2008 applications in parallel, Carter said. AWS will pay for one of those licenses during the upgrade process, which gives the cloud leader a selling point when bidding for Windows Server 2008 customers.

Because of its size, enjoying roughly double the cloud market share of Microsoft Azure, AWS actually runs more Windows workloads in the cloud than Microsoft does, Carter said. AWS also plans to tout its reliability ratings in its push for Windows Server 2008 workloads, after Microsoft’s rough year for cloud uptime in 2018.

The path is a little clearer for customers looking to move SQL Server 2008 data to the cloud, given the managed SQL Server cloud database services that all cloud vendors offer. They’ll all support companies that want to manage their own newer editions of SQL Server databases, but moving to a managed database makes life easier in many ways.

I’ll take you there

This deadline also presents opportunities for a wide range of cloud service providers.

Companies that lack technical expertise often contract with consultants and resellers who can do a lot of the heavy lifting for them, promising to make the transition as painless as possible for a modest fee. And other infrastructure tool providers can also get in on the action: Chef announced a Windows migration tool at ChefConf earlier this month that it said would make this process much easier.

Skytap is another option for companies that need to deal with this end-of-support deadline. Skytap’s whole mantra involves “modernizing traditional applications,” moving ancient applications to its own cloud and managing the tricky parts for its clients.

There are plenty of customers out there that don’t have a complete plan in place yet.

“There are plenty of customers out there that don’t have a complete plan in place yet,” said Karri Alexion-Tiernan, senior vice president of product marketing for Skytap. “Most organizations that we work with are limited in the dev and test services they have available,” she said, referring to the process of making sure applications will run reliably on production systems.

All of this adds up to a big upgrade opportunity for cloud providers. The cloud revolution was well underway when the last major Windows Server upgrade deadline passed in 2015, but there were still lots of companies that weren’t ready to make that leap for any number of reasons.

In 2019, they have less justification for avoiding the clear value proposition presented by cloud computing. The next six months are going to be an extremely competitive time period for cloud vendors, consulting firms, and others scrambling to get a piece of this big migration opportunity.

The growth of sophisticated hybrid cloud products and services has allowed large corporations with mission-critical applications running on old technology to postpone the inevitable, but every company has its breaking point. This process of “digital transformation” has driven the marketing budgets of big tech companies for several years now, and by the time cloud providers report their financial results next January, we’ll start to get a sense of just how big this opportunity was.

[Editor’s note: This post was updated to clarify the benefits of moving to a managed database.]