Few products are as mission critical to most organizations IT as Windows Server™. Many, if not most, are currently running the 2016 edition, but there are still a significant number using Windows Server 2008 or Windows Server 2008 R2. According to the Microsoft® Lifecycle Policy, Extended Support for the 2008 editions will end on January 14, 2020, which means Microsoft will no longer provide security updates. This will come as no surprise to most, and many impacted organizations are already planning for their upgrade. The part that might surprise them, however, will be the pressure Microsoft will impose to motivate them to move at least part of their IT to the cloud. Microsoft has been very public about their desire to move their customers to the cloud, but organizations who are still using Windows Server 2008 represent a particularly unique opportunity for Microsoft. These customers may be relatively slow to upgrade, and there is a good chance their on-prem servers and hardware may be older and in need of replacement. Microsoft will use these factors to remind them of the benefits of Azure and other cloud services, whether with a complete migration or a hybrid environment. This can work to your benefit if the customer organization is even considering moving to the cloud, as Microsoft will probably offer attractive terms and incentives. Unfortunately, the alternative may work against organizations, as MS is less accommodating for those wishing to remain solely on-premises.
It’s worth noting that those who take advantage of Microsoft’s goal of moving them to the cloud may not receive similar terms when it’s time to renew their agreements. We have seen many instances where customers were offered very aggressive discounts to get them to move, but once that goal has been achieved, future discounts are much less attractive.