Migration to the cloud has rapidly become a core strategic goal for enterprises that hope to stay competitive in the age of artificial intelligence, advanced analytics, and hybrid work environments. As organizations re-evaluate their infrastructure choices, a dramatic shift is underway—accelerated by recent changes in the virtualization market. Microsoft is stepping up its efforts to attract VMware customers with an ambitious expansion of incentives, technical programs, and AI-laden cloud tools, positioning its Azure platform as the preferred destination for those seeking to modernize IT while sidestepping the turbulence unleashed by new VMware owner Broadcom.
The context for this wave of migrations is rooted in Broadcom’s $69 billion acquisition of VMware in late 2023, a move that has introduced sweeping changes to VMware’s pricing, partner programs, and product support. Many organizations—especially those with significant on-premises investments—have been caught off guard by steep cost increases and new licensing models. According to industry analysts and testimony from system integrators, these disruptions are prompting IT leaders across industries to conduct “explore the alternatives” exercises at an unprecedented scale.
Chris Bogan, VP of Sales at Mark III Systems, shared with CRN that, “There’s definitely a lot of folks that, with [VMware’s] new pricing, are looking to go explore what the alternatives are.” This sentiment is widely echoed within the IT community: customers are questioning the value proposition of staying with VMware given both direct cost impacts and broader concerns about agility, support, and ecosystem stability.
The expanded set of migration incentives falls within the broader context of Microsoft’s 2026 fiscal year investment strategy, which features a reported 20% year-over-year boost in enterprise customer investment funds. While Microsoft has not disclosed detailed numbers for the VMware migration program specifically, it is clear that these funds include substantial allocations for migration activities. The ultimate aim: lower the friction, risk, and cost for organizations migrating their VMware workloads while catalyzing downstream adoption of Azure-native apps, services, and AI offerings.
Dezen’s comments during a recent interview serve as a clarion call to Microsoft partners: “I think every customer that wants to participate in all of the magic of AI, first and foremost, needs to be migrated to the cloud. That is absolutely the call to action for all of our partners.” She reinforced that the path to Azure unlocks not just technical parity with legacy virtualization platforms but a “one-stop shop” for end-to-end modernization: infrastructure, applications, data, AI, and Microsoft’s robust, market-leading security posture.
Key elements of Azure Accelerate include:
“We see some of the left-behind VMs that are out there. That’s the projects that we have going on: things that they didn’t know what to do with,” said Goldstein. But as more customers voluntarily test Azure’s capabilities, the results are winning over skeptics. “We found a lot of VMware customers dip their foot into Azure, and they realize, ‘Wow, this is pretty amazing.’ And I think they’re just looking to bring the rest over.”
Another key factor driving migrations—especially in disaster-prone regions or where uptime is critical—is the superior resilience and geographic redundancy offered by large-scale public cloud platforms. Goldstein points out, “In South Florida, we’re getting bombarded [by storms], so I think a lot of people are starting to think that finally the cloud is the way to go.” Azure’s global infrastructure is a clear draw for those seeking to reduce reliance on local, vulnerable datacenters.
Cloud-based workload migration also opens the door to a new class of AI-enabled services—from Azure OpenAI integrations to native analytics, automation, and decision intelligence tools. These are unavailable, or far more difficult and expensive to implement, in on-premises VMware settings. Dezen underscores this: “The benefit to a customer to move their all of their services and solutions to Azure is you truly get the one-stop shop, and we have a wealth of partner capability designed to meet customer needs across their entire stack, from infrastructure, to their apps and services, to data and AI, and, of course, all encompassed by market-leading security.”
Based on the information available, Microsoft’s migration incentives can include:
Microsoft’s ramped-up migration initiative comes exactly as organizations feel the pinch from VMware’s pricing and program changes under Broadcom’s stewardship. The timing allows Microsoft to frame Azure not just as a technical option but as a relief valve for IT and financial concerns.
2. Deep Partner Ecosystem
The Microsoft AI Cloud Partner Program and companion initiatives provide a mature channel to support, educate, and share risk with enterprise customers—a point repeatedly stressed by Microsoft executives and partner CEOs alike.
3. Innovation and Value Beyond Virtualization
Azure’s ability to serve as a launchpad for cutting-edge AI, advanced analytics, and seamless app modernization is a leap ahead compared to “lift-and-shift” strategies that merely swap one hypervisor for another.
Despite enthusiasm, not all workloads or organizations are viable candidates for cloud migration. As Bogan notes, “moving to the cloud has been a non-starter for customers who require on-premises data centers for security reasons.” This is especially relevant in industries or geographies with strict regulatory control. While Azure Stack and hybrid deployments offer alternatives, these require additional planning and, at times, compromise.
2. Potential for Over-Promising
Microsoft’s promises of seamless migration and “magic of AI” post-migration, while appealing, should be tempered by the operational complexity of large-scale migrations—especially for organizations with aging infrastructure, bespoke workloads, or highly customized VMware deployments. Peer-reviewed case studies and independent technical validations will remain essential proof points as these projects ramp up.
3. Licensing and Cost Transparency
Some community feedback reflects persistent confusion about Microsoft’s licensing—especially with respect to re-using Windows 10 (or 11) keys in VMware scenarios, volume licensing nuances, and region-specific legalities. Any migration strategy must include a thorough review of licensing posture, ideally with pre-approved documentation from Microsoft’s legal or compliance teams to avoid downstream disputes.
4. Risk of Single-Vendor Dependency
Committing entirely to the Azure ecosystem, while conferring many advantages, introduces a new vendor lock-in risk. Customers should weigh this against the perceived or real risk of remaining with VMware/Broadcom, and may wish to maintain a hybrid or multi-cloud approach where possible.
Others urge caution, emphasizing the importance of proactive planning, pilot projects, and maintaining communication with account representatives to avoid costly missteps. Volume licensing, transparent activation management, and legal compliance with Microsoft’s policies surface again and again as non-negotiables in any serious migration effort.
The friction in switching virtualization vendors or platforms remains very real. Yet, with the right mix of incentives, technical support, and customer advocacy, Microsoft is shaping itself as a frontrunner. The coming year will be critical in seeing how many organizations heed the call—and whether the promise of migration magic truly materializes, or whether hidden complexities and new dependencies slow the stampede.
For IT leaders and decision makers, the message is clear: now is the time to scrutinize your virtualization roadmap, re-examine total cost of ownership (TCO) under the new VMware regime, and engage with trusted migration partners. Whether your destination is public cloud, hybrid, or a next-generation on-premises stack, this is a migration wave that demands both urgency and caution. With cloud and AI moving from buzzwords to business imperatives, those who hesitate may soon find themselves struggling to catch up.
Source: CRN Magazine Microsoft Is ‘Investing More In VMware Migrations This Year,’ Dezen Says
The Broadcom-VMware Upheaval: A Catalyst for Migration
The context for this wave of migrations is rooted in Broadcom’s $69 billion acquisition of VMware in late 2023, a move that has introduced sweeping changes to VMware’s pricing, partner programs, and product support. Many organizations—especially those with significant on-premises investments—have been caught off guard by steep cost increases and new licensing models. According to industry analysts and testimony from system integrators, these disruptions are prompting IT leaders across industries to conduct “explore the alternatives” exercises at an unprecedented scale.Chris Bogan, VP of Sales at Mark III Systems, shared with CRN that, “There’s definitely a lot of folks that, with [VMware’s] new pricing, are looking to go explore what the alternatives are.” This sentiment is widely echoed within the IT community: customers are questioning the value proposition of staying with VMware given both direct cost impacts and broader concerns about agility, support, and ecosystem stability.
Microsoft’s Strategic Response: Doubling Down on VMware Migrations
Recognizing the moment, Microsoft is “investing more in VMware migrations this year,” said Nicole Dezen, Chief Partner Officer at Microsoft. The company is not only expanding its portfolio of technical migration tools, but also ramping up financial incentives and partner funding aimed at accelerating the exodus from VMware to Azure.The expanded set of migration incentives falls within the broader context of Microsoft’s 2026 fiscal year investment strategy, which features a reported 20% year-over-year boost in enterprise customer investment funds. While Microsoft has not disclosed detailed numbers for the VMware migration program specifically, it is clear that these funds include substantial allocations for migration activities. The ultimate aim: lower the friction, risk, and cost for organizations migrating their VMware workloads while catalyzing downstream adoption of Azure-native apps, services, and AI offerings.
Dezen’s comments during a recent interview serve as a clarion call to Microsoft partners: “I think every customer that wants to participate in all of the magic of AI, first and foremost, needs to be migrated to the cloud. That is absolutely the call to action for all of our partners.” She reinforced that the path to Azure unlocks not just technical parity with legacy virtualization platforms but a “one-stop shop” for end-to-end modernization: infrastructure, applications, data, AI, and Microsoft’s robust, market-leading security posture.
Azure Accelerate: Microsoft’s Offensive Against VMware Lock-In
One of Microsoft’s newest plays in the migration market is Azure Accelerate—a comprehensive initiative bundling migration assets, technical enablement, and expanded partner incentives. According to Dezen, this program is designed not just to get workloads off VMware, but to set customers up for long-term success with cloud-based data, apps, and AI-driven innovations. Azure Accelerate leverages Microsoft’s ongoing investments in automation, assessment tools, and hybrid management, offering tailored migration journeys whether a customer’s current environment is partly in the cloud, all on-premises, or highly regulated.Key elements of Azure Accelerate include:
- Automated Assessment & Planning: Tools to evaluate VMware environments, inventory assets, and create detailed migration plans.
- Technical Migration Workshops: Guidance and hands-on labs delivered by certified partners and Microsoft engineers.
- Expanded Financial Incentives: Credits and funding to lower migration costs and offset potential overages or unexpected technical hurdles.
- Post-Migration Enablement: Support for optimizing workloads post-migration to take full advantage of Azure-native capabilities, especially AI and advanced analytics.
Customer Case Studies: From Caution to Cloud Confidence
Microsoft’s bid to win over VMware customers rests not only on incentives but also on proof: demonstrating successful outcomes for organizations facing tough choices. Michael Goldstein, CEO of Microsoft gold partner LAN InfoTech, highlighted one common pain point—dealing with “second-tier workloads” or “left-behind VMs” for which migration paths were previously unclear or cost-prohibitive.“We see some of the left-behind VMs that are out there. That’s the projects that we have going on: things that they didn’t know what to do with,” said Goldstein. But as more customers voluntarily test Azure’s capabilities, the results are winning over skeptics. “We found a lot of VMware customers dip their foot into Azure, and they realize, ‘Wow, this is pretty amazing.’ And I think they’re just looking to bring the rest over.”
Another key factor driving migrations—especially in disaster-prone regions or where uptime is critical—is the superior resilience and geographic redundancy offered by large-scale public cloud platforms. Goldstein points out, “In South Florida, we’re getting bombarded [by storms], so I think a lot of people are starting to think that finally the cloud is the way to go.” Azure’s global infrastructure is a clear draw for those seeking to reduce reliance on local, vulnerable datacenters.
Security, AI, and the ‘One-Stop Shop’ Value of Azure
Security remains a pivotal concern for enterprise IT leaders, particularly those in regulated industries or with heightened privacy/compliance obligations. Critics of cloud migration long pointed to data sovereignty and control as barriers. However, Microsoft is positioning Azure as a secure “one-stop shop,” touting its record on compliance certifications, built-in encryption, and investments exceeding $1 billion in cybersecurity annually.Cloud-based workload migration also opens the door to a new class of AI-enabled services—from Azure OpenAI integrations to native analytics, automation, and decision intelligence tools. These are unavailable, or far more difficult and expensive to implement, in on-premises VMware settings. Dezen underscores this: “The benefit to a customer to move their all of their services and solutions to Azure is you truly get the one-stop shop, and we have a wealth of partner capability designed to meet customer needs across their entire stack, from infrastructure, to their apps and services, to data and AI, and, of course, all encompassed by market-leading security.”
Financial Perspective: Costs, Incentives, and the Migration ROI
A central argument for migration revolves around cost: what will a move cost, how quickly can it be amortized, and what are the hidden expenses? While Broadcom’s VMware pricing changes have introduced new and sometimes steep costs for maintaining the status quo, Microsoft’s answer is a blend of direct and indirect incentives.Based on the information available, Microsoft’s migration incentives can include:
- Direct discounts on Azure compute and storage for migrated workloads
- “Bridge” support for licensing continuity during the migration process
- Funding for technical consulting, planning, and proof-of-concept pilots
- Access to enterprise investment funds that in 2025 saw a 20% year-over-year increase
Critical Analysis: Notable Strengths and Remaining Risks
Strengths
1. Strategic Timing and Addressing Customer PainMicrosoft’s ramped-up migration initiative comes exactly as organizations feel the pinch from VMware’s pricing and program changes under Broadcom’s stewardship. The timing allows Microsoft to frame Azure not just as a technical option but as a relief valve for IT and financial concerns.
2. Deep Partner Ecosystem
The Microsoft AI Cloud Partner Program and companion initiatives provide a mature channel to support, educate, and share risk with enterprise customers—a point repeatedly stressed by Microsoft executives and partner CEOs alike.
3. Innovation and Value Beyond Virtualization
Azure’s ability to serve as a launchpad for cutting-edge AI, advanced analytics, and seamless app modernization is a leap ahead compared to “lift-and-shift” strategies that merely swap one hypervisor for another.
Risks and Caveats
1. On-Premises Holdouts and Regulatory ConstraintsDespite enthusiasm, not all workloads or organizations are viable candidates for cloud migration. As Bogan notes, “moving to the cloud has been a non-starter for customers who require on-premises data centers for security reasons.” This is especially relevant in industries or geographies with strict regulatory control. While Azure Stack and hybrid deployments offer alternatives, these require additional planning and, at times, compromise.
2. Potential for Over-Promising
Microsoft’s promises of seamless migration and “magic of AI” post-migration, while appealing, should be tempered by the operational complexity of large-scale migrations—especially for organizations with aging infrastructure, bespoke workloads, or highly customized VMware deployments. Peer-reviewed case studies and independent technical validations will remain essential proof points as these projects ramp up.
3. Licensing and Cost Transparency
Some community feedback reflects persistent confusion about Microsoft’s licensing—especially with respect to re-using Windows 10 (or 11) keys in VMware scenarios, volume licensing nuances, and region-specific legalities. Any migration strategy must include a thorough review of licensing posture, ideally with pre-approved documentation from Microsoft’s legal or compliance teams to avoid downstream disputes.
4. Risk of Single-Vendor Dependency
Committing entirely to the Azure ecosystem, while conferring many advantages, introduces a new vendor lock-in risk. Customers should weigh this against the perceived or real risk of remaining with VMware/Broadcom, and may wish to maintain a hybrid or multi-cloud approach where possible.
Competitive Landscape: More Than Just Microsoft vs. VMware
Although Microsoft is the most aggressive in courting VMware migrations, it is not alone. Amazon Web Services (AWS), Google Cloud, and newcomers such as Nutanix and HPE GreenLake are all looking to capture their share of disaffected VMware workloads. HPE VM Essentials, cited as a “massive opportunity” by some partners, targets midsized organizations seeking a VMware alternative without a big-bang move to the public cloud. Each provider touts a different mix of cost, flexibility, and migration tooling.Community Insights: Real-World Perspectives
A scan of IT forums reveals a robust debate on the merits of VMware-to-cloud migrations. Users report on the practicalities of licensing, backup, and performance, echoing concerns about speed, cross-border legalities, and the technical realities of moving legacy applications. Some highlight Microsoft’s long track record of partnering with global value-added resellers and the ability to negotiate custom license images and discount pricing for large enterprises.Others urge caution, emphasizing the importance of proactive planning, pilot projects, and maintaining communication with account representatives to avoid costly missteps. Volume licensing, transparent activation management, and legal compliance with Microsoft’s policies surface again and again as non-negotiables in any serious migration effort.
What’s Next: The Future of Virtualization and Cloud Migration
The acceleration of VMware migrations represents one chapter in the broader story of cloud transformation. As AI-powered infrastructure, security, and automation become baseline expectations, organizations will increasingly be forced to modernize—not just to avoid penalties but to access the innovations that drive revenue and operational agility. Microsoft’s expanded investments and incentives in the VMware migration space are significant, but their lasting value will be measured in the ability to deliver seamless, secure, and future-proof outcomes across the full range of customer needs.The friction in switching virtualization vendors or platforms remains very real. Yet, with the right mix of incentives, technical support, and customer advocacy, Microsoft is shaping itself as a frontrunner. The coming year will be critical in seeing how many organizations heed the call—and whether the promise of migration magic truly materializes, or whether hidden complexities and new dependencies slow the stampede.
For IT leaders and decision makers, the message is clear: now is the time to scrutinize your virtualization roadmap, re-examine total cost of ownership (TCO) under the new VMware regime, and engage with trusted migration partners. Whether your destination is public cloud, hybrid, or a next-generation on-premises stack, this is a migration wave that demands both urgency and caution. With cloud and AI moving from buzzwords to business imperatives, those who hesitate may soon find themselves struggling to catch up.
Source: CRN Magazine Microsoft Is ‘Investing More In VMware Migrations This Year,’ Dezen Says
