Overview

Background

The ease of server creation in a virtualised environment has resulted in hundreds of instances. These servers all face an end of life and loss of support from the vendor, leaving them open to increased support costs and susceptibility to attack from malware as security updates are stopped. At the time of writing it is assumed that the next version of the server OS will be known as Windows Server 2016. By the time server 2016 is available we will have just around three and a half years to upgrade Windows 2008 to remain in a supported state. This project is to plan and implement an upgrade of all of the Windows server estate to a supported level by the end of 2019.

Scope

Over three hundred Windows 2008 servers to migrate by the end of 2019.

Objectives

Upgrade all servers to a supported OS before the end of life of Server 2008.

Implement lifecycle management for all servers/services - this means having an agreed plan to move them to the next OS version on an agreed date

Deliverables

Windows Server 2016 deployed and supported

Removal of all Windows 2008 server from network

Lifecycle management for all servers/services established

Benefits

Stay supported by Microsoft. Premier support is expensive. Allowing servers to fall out of support while continuing to pay Premier is not cost effective.

Continue to receive security and critical updates. The latest OS has additional security tools and enhancements based on previous experience.  Failure to upgrade will mean no security updates putting the server and other infrastructure at risk from attack and data loss.

Stay Compliant - avoid financial and legal penalties.

Opportunity to modernize - learn about new tools that could help us to work more efficiently.

Business Resiliency – more reliable and stable OS.

Better integration with cloud.

Reduce support costs. It is costly having staff supporting multiple operating systems. The longer an OS takes to disappear from our infrastructure, the more problematic it becomes to support due to reduced exposure to the OS as numbers dwindle. Knowledge becomes difficult to retain in support of ageing systems. Support of such systems becomes more expensive as time goes on.

Being forced to upgrade as a result of applications and OS no longer being supported is costly and inefficient when compared to a planned upgrade.

A successful upgrade takes time. Testing takes time to ensure there are no security holes or issues with the configuration. Waiting to the last minute to start considering options is unwise. Work on migration plans should start now. The upgrade may not be smooth and testing may shine a light on a number of incompatibilities for business critical software. Recognising and taking steps to address this possibility in a timely and planned manner will pay dividends.

Success Criteria

No Windows Server in running live in an unsupported state by the end of 2019.