As businesses race to innovate, modernize, and stay competitive, one thing becomes clear—legacy infrastructure is holding them back. That’s why companies are choosing Microsoft Azure—a future-ready cloud platform that supports Windows, SQL Server, VMware, and Linux migrations with built-in security, AI-ready infrastructure, and cost-saving advantages.

At Oakwood, we go beyond simple cloud migrations. Our approach ensures that organizations don’t just move to the cloud—they transform their operations, cut costs, modernize applications, and drive AI-powered innovation.

The shift to the cloud isn’t about technology alone. It’s about unlocking better performance, tighter security, lower costs, and AI-driven innovation. For many of our clients, their move to Azure has been the turning point in their digital transformation journey.

Leaving Legacy Behind

In nearly every cloud migration conversation we have, the same pain points come up. Businesses are stuck dealing with aging infrastructure, unpredictable licensing costs, and security challenges—and they’re tired of constantly managing upgrades and patches.

For some, the motivation to migrate is clear: their on-prem Windows Server or SQL Server environments are hitting end-of-support. They don’t want to face the compliance risks (or the massive price tag of an infrastructure refresh). For others, it’s about the need for greater agility—to scale workloads, integrate AI, or take advantage of cloud-native capabilities without being locked into expensive, inflexible models.

Regardless of the starting point, the goal is the same: move smarter, save costs, and set the stage for innovation.

The VMware Challenge

Lately, many of our clients running VMware environments have come to us with growing concerns. Since Broadcom’s acquisition of VMware, the conversation has shifted from “Should we migrate?” to “How soon can we migrate?”.

The customers we work with often tell us about:

• Skyrocketing costs due to new subscription-only licensing models
• Support uncertainty, with fears about VMware’s long-term roadmap
• Operational headaches, especially for organizations trying to run hybrid workloads

For years, VMware environments provided businesses with a solid virtualization foundation. But now, many organizations are questioning whether staying the course is worth the cost and risk. That’s where Azure VMware Solution (AVS) comes in.

With AVS, we’ve helped businesses move VMware workloads to Azure without disrupting operations. They can continue using the same VMware tools they’re familiar with, but with Microsoft’s cloud scalability, security, and cost advantages. And unlike VMware’s shifting licensing landscape, Azure offers predictable, long-term pricing—a relief for many IT leaders.

If Broadcom’s changes have left you rethinking your VMware strategy, you’re not alone. We’ve already helped organizations make the transition smoothly, and we can help you do the same.

Windows & SQL Server Migrations

For businesses running Windows Server and SQL Server, the challenges are different—but just as pressing. We’ve worked with companies that have held onto their on-prem environments for too long, thinking they could squeeze a few more years out of their infrastructure. But as end-of-support deadlines approach, many realize the risks far outweigh the benefits.

Security is usually the biggest concern. Without ongoing updates, legacy Windows and SQL Server environments become prime targets for cyber threats. Compliance issues arise, and IT teams find themselves spending more time putting out fires than focusing on innovation.

One of the first things we tell clients in this situation is that moving to Azure isn’t just a defensive move—it’s an opportunity. With Azure Hybrid Benefit, organizations can save up to 80% on Windows and SQL licensing costs. Plus, Azure provides free extended security updates, meaning businesses don’t have to scramble to replace aging infrastructure.

And the performance benefits? Immediate. We’ve seen workloads that struggled on-prem gain significant speed and efficiency in Azure, with built-in automation and AI-powered optimization making day-to-day operations easier.

For IT teams that have been managing Windows and SQL environments for years, migration can feel like a heavy lift. But that’s why we’ve built a structured, proven process that makes the transition seamless—whether it’s a full lift-and-shift, a phased modernization, or a hybrid approach.

Linux Workloads

While some businesses are focused on modernizing their Windows environments, others are looking to migrate and optimize Linux-based applications. We’ve worked with teams who are deeply invested in open-source ecosystems, and their primary concern isn’t just moving to the cloud—it’s making sure they can maintain flexibility, performance, and cost efficiency.

Azure has quietly become one of the best platforms for running Linux workloads. It supports all major distributions—Ubuntu, Red Hat, Debian, SUSE, and more—and offers specialized HPC instances, Kubernetes support, and AI-ready compute options.

One of the biggest benefits we’ve seen for Linux-based organizations is Azure Hybrid Benefit for Linux, which allows businesses to bring their existing Linux licenses to Azure, reducing costs significantly. And with Azure Arc, companies can manage their Linux workloads across on-prem, hybrid, and multi-cloud environments with a single control plane.

For Linux-heavy organizations, Azure isn’t just another cloud provider—it’s a performance-driven, AI-ready platform that helps them scale faster and smarter.

Oakwood’s Migration Approach

If there’s one thing we’ve learned from migrating workloads to Azure, it’s that no two migrations are the same. Some organizations need a quick lift-and-shift, while others require a more strategic, phased approach. That’s why Oakwood’s migration methodology is tailored to your business needs, ensuring a secure, cost-effective, and high-impact transition.

We’ve worked with companies at every stage of the cloud journey—from those taking their first steps into Azure to enterprises optimizing complex hybrid environments. No matter where you are, we help you:

• Develop a migration roadmap that aligns with your business objectives
• Optimize costs and licensing to maximize ROI
• Ensure security and compliance throughout the migration process
• Modernize applications and unlock AI capabilities post-migratio

Is it time for YOU to migrate?

For many businesses, the cloud is no longer a question of if, but when and how. Whether you’re looking to escape VMware’s licensing model, modernize Windows & SQL, or optimize Linux workloads, Oakwood is ready to guide you through the process.

We’ve done this before. We know the challenges, and more importantly, we know how to solve them.

If you’re ready to migrate—and innovate—let’s start the conversation today.