1. The first reason to upgrade Windows Server 2008 is that the team has the capacity – and the focus right now. Things have slowed down, people are working at home and are actually hungry for a meaningful, measurable project.
2. It’s an opportunity to review your company’s software and apps to be sure they are compatible with the new server. Take a full inventory and align your migration strategy with where your business will need to be in the future.
3. It’s time to clean up technical debt, capture tribal knowledge and catalog all servers, applications and dependencies on WS2008.
4. It’s an opportunity to switch to a cloud-based solution which makes your IT team more agile and able to adapt new technology.
5. You don’t want to put the organization’s security at risk. Your version of the software will not be provided with any more security updates.
6. Your data and systems are much more vulnerable to malware and viruses.
7. It will cost you more to have to adapt custom security measures and maintain poor performing and incompatible applications. Legacy maintenance is typically 80% of IT budgets – and is both expensive and a drain on innovation.
8. You could fall behind your competitors. Windows Server 2008 R2 was built for a different world, and as such, it’s missing many features included in its successors. Microsoft has many new features, including Azure network adaptor support, unified management in Windows Admin Center and enhanced Windows Defender Advanced Threat Protection. While not all of them will be needed in every environment, not having access to new features raises the risk of eventually falling behind competitors or suffering unforeseen technical, financial and logistical hurdles.
9. You may fall out of compliance with industry regulations which require and even assume a more current OS.
10. There are solutions to make this a manageable and satisfying step forward for your IT team. They will learn new things about their own environment, the business’s priorities, and build their skills.
There’s never been a more important time to upgrade Windows Server 2008 to Azure.
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