Why I’m Transitioning from VMware to Microsoft Hyper-V: A CIO’s Perspective

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As the CIO of a forward-thinking organization, I’ve always prided myself on staying ahead of the curve when it comes to technology and infrastructure. My journey with VMware has been a significant part of that story.

For years, I have been a staunch supporter of VMware, having achieved certifications as a VMware architect and NSX architect and being recognised as a vExpert for five consecutive years. My expertise in VMware has been instrumental in building resilient, scalable infrastructures that have supported our business through various growth phases.

However, the technology landscape is ever-evolving, and with it, so too are the tools and platforms we rely on. Recent changes within VMware, particularly following its acquisition, have led me to reassess our technology stack. The changes in licensing models and cost structures have been the most significant triggers for this reevaluation. What was once a straightforward and relatively transparent licensing process has become increasingly complex and, frankly, more expensive. This shift has put considerable pressure on our IT budget and has made it challenging to justify continuing with VMware under these new terms.

In addition to the licensing and cost challenges, VMware’s recent website redesign has introduced a new layer of complexity. The revamped interface, while modern in appearance, has made it frustratingly difficult to locate critical information, updates, and tools. For a platform as central to our operations as VMware, easy and reliable access to resources is non-negotiable. This added friction in accessing essential tools and information has only compounded our growing concerns about continuing with VMware.

Faced with these challenges, I began exploring alternatives that could better align with our strategic goals and provide a more streamlined, cost-effective solution. This exploration led me to Microsoft Hyper-V. As an ex-MVP in multi-cloud categories, I’ve long been aware of the strengths and capabilities of Hyper-V, particularly its seamless integration with Azure. This integration offers a cohesive environment that allows us to consolidate our workloads within the Azure ecosystem, providing a level of simplicity and peace of mind that is increasingly hard to find.

An additional factor that influenced our decision was the expertise and alignment of our IT team with Microsoft platforms. Our team already possesses strong knowledge and experience with Microsoft technologies, which positions us well for managing a Hyper-V environment. This familiarity with the Microsoft ecosystem will make it easier for our team to adopt Hyper-V quickly and confidently, ensuring a smoother transition and more efficient management of our infrastructure.

The decision to transition from VMware to Hyper-V was not made lightly, but it became clear that it was the right move for our organization. The advantages of Hyper-V, particularly in conjunction with Azure, provide a compelling case for change. The ability to manage our infrastructure in a more integrated and cost-effective manner, combined with the stability and reliability of Microsoft’s platforms, made the decision to migrate much easier.

It’s important to recognize that VMware remains a strong platform with many benefits. However, the recent changes in cost, licensing, and the user experience have tipped the scales. For us, moving to Hyper-V was a logical step in ensuring that our IT infrastructure remains robust, agile, and aligned with our long-term strategic goals.

In my next article, I’ll be sharing insights from our migration journey—detailing the challenges we encountered, the strategies we employed to overcome them, and the key lessons we learned along the way. Whether you’re considering a similar transition or simply interested in the process, I believe there will be valuable takeaways for all.

Stay tuned for more on how we navigated this significant change and what it means for the future of our IT infrastructure.

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[…] This blog post will dive into the advantages of making the switch to Hyper-V on Windows Server 2025 and examine how VMware’s recent changes have prompted many organisations to rethink their reliance on VMware. For further context, we’ll reference an insightful article from Cloudoasis, “Why I’m Transitioning from VMware to Microsoft Hyper-V: A CIO’s Perspective. […]

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