After ILTACON 2026: Why Evolving from VMware Starts with Better Business Decisions
ILTACON 2026 brought the legal technology community back to the Gaylord Opryland in Nashville for peer-driven education, practical programming, business partner conversations, and face-to-face networking. Now that the conference has wrapped, Kraft Kennedy is continuing the conversation, reflecting on the issues that matter most to law firm technology leaders.
In this blog, we’ll touch back on Dominick Ciacciarelli’s ILTACON session, “Evolving from VMware,” and move forward into the broader business decisions firms should be making in response to the changing virtualization landscape.
From Tech Sessions to Firm Environments
Technical topics such as VMware have long formed the quiet foundation beneath many law firm technology environments. They are not always visible to attorneys, administrators, or firm leaders, but they support the systems legal organizations depend on every day. After ILTACON, Beth Anne Stuebe sat down with Dominick to revisit the key themes from his session and discuss why the VMware conversation now belongs in a broader business planning context.
Since Broadcom’s acquisition of VMware, legal technology leaders have faced a changed licensing and planning landscape. The move from perpetual licensing toward subscription, the reduction of VMware’s product catalog into fewer bundled offerings, and the shift toward per-core metrics with minimum purchase thresholds have altered the economics behind a platform many firms once treated as a default.
For law firms, this is no longer just a procurement annoyance or an infrastructure refresh. It is a strategic planning issue with consequences for cost, business continuity, auditability, security, staffing, and the firm’s long-term technology direction.
At ILTACON 2026, Dom led this conversation during his session, “Evolving from VMware.” The discussion focused on how legal organizations can evaluate available paths with the technical discipline, financial context, and operational realism needed to make the right call for their environment.
VMware Was the Default. Now Firms Need a Decision Framework
When technology is working, it is easy to underestimate how much depends on it. Virtualization sits beneath some of the most important systems in a legal environment, including document management, matter-centric file services, identity controls, eDiscovery tools, and remote access platforms.
That dependency makes the current VMware conversation especially urgent. Recent licensing changes have created new pressure around renewals, subscription compliance, minimum core requirements, and bundled features firms may not fully need. In some environments, especially smaller or right-sized clusters, those changes can turn a predictable infrastructure cost into a significant and unexpected financial jump.
One of the strongest takeaways from the session was that firms need to move past the reactive question, “What do we replace VMware with?” and toward a more useful one.
What Operating Model Should Our Firm be Building Toward?
One of the most important points Dom is that this conversation should not be confined to the infrastructure team. Technical implementers need to be involved, but so do finance leaders, firm administrators, and executives responsible for budgeting, risk, and long-term planning.
That is because every option carries financial consequences.
Staying with VMware may require accepting new licensing terms or higher subscription costs. Moving away from VMware may involve assessment work, migration planning, staff retraining, new tools, and changes to backup, disaster recovery, monitoring, and support processes. Moving to cloud infrastructure may also change the type of spending involved, potentially shifting costs from capital expense to operating expense.
In other words, this is not simply a platform decision. It is a cost-model decision, a risk-management decision, and an operational-readiness decision.
For CFOs, executive directors, firm administrators, and technology leaders, “Evolving from VMware” highlighted an important reality: successful transformation starts with the right questions. Before evaluating platforms, allocating budget, or planning a migration, firms need a clear understanding of their goals, risks, and long-term operating model.
The Three Paths Firms Should Be Evaluating
There are three credible paths for organizations evaluating life after VMware: remain on-premises with another hypervisor, such as Hyper-V, move workloads to Azure IaaS, or modernize toward PaaS and SaaS models that reduce server management responsibilities.
Each path has advantages and tradeoffs.
- Staying on-premises
This might be the most direct replacement path for firms that want to preserve local control, maintain data residency, and continue supporting workloads that depend on low-latency on-premises infrastructure. But this is not a simple format conversion. Firms still need to revalidate high availability, backup, disaster recovery, monitoring, patching, and administrative processes.
- Migrating to Azure IaaS
While this could appeal to firms that want to move away from hardware lifecycle management and private virtualization operations, a lift-and-shift migration is only the first step. The longer-term value typically comes from strengthening security controls, improving resilience, using automation, and re-platforming where appropriate.
- Modernizing toward PaaS or SaaS
Considered a durable long-term response for firms that want to reduce their dependence on infrastructure altogether. “Serverless” does not mean there are no servers; it means the firm is no longer responsible for sizing, patching, licensing, or managing the hypervisor beneath them.
The right answer may be a hybrid of all three.
Start with Assessment Before Selecting a Platform
This is why Dom’s approach starts with assessment rather than platform selection.
Before choosing a destination, firms need to understand what they are running today. That means inventorying applications, identifying workload dependencies, assessing performance and latency requirements, reviewing vendor support constraints, and determining which systems need to remain on virtual machines versus which could be rehosted, re-platformed, refactored, or replaced.
The ILTACON session offered a practical decision framework: start with the constraints and the calendar. Renewal dates, hardware end-of-life deadlines, colocation contracts, disaster recovery agreements, circuit commitments, and budget cycles can all force the timing. From there, firms should ask what risk comes with doing nothing, which workloads are ready to modernize, which must remain on VMs, and what operating model the organization can realistically support.
Those questions matter because the wrong migration path can create as much risk as the licensing problem it was meant to solve.
Beyond infrastructure, the session emphasized the operational and security capabilities that must accompany any migration effort, including identity management, cybersecurity, incident readiness, hybrid cloud operations, modern management tools, and evidence preservation.
That framing is important for legal organizations because a virtualization migration cannot stop at compute and storage. Firms also need to preserve defensibility, auditability, and operational maturity as workloads move.
If workloads move, security controls must move with them. Identity and access models need to be redesigned or validated. Backup and disaster recovery plans need to be retested. Monitoring and management tools may need to change. Incident response runbooks need to reflect the new environment.
Cloud adoption has been underway for years, but VMware’s licensing changes have accelerated the need to revisit the operating model. At the same time, AI, identity, and single sign-on are raising expectations for how infrastructure should support secure, flexible, and well-governed legal work.
This makes this session about more than VMware: it is about where legal infrastructure is headed in 2026 and beyond.
Key Takeaways from “Evolving from VMware”
The 2026 session gave attendees a practical, decision-focused discussion centered on their unique needs and priorities, not a sales presentation or a generic technical recommendation.
Dom and the panel helped attendees compare cloud-based, on-premises, and hybrid virtualization strategies; understand the planning work needed before migration; think through identity and security implications; and evaluate the tooling required to move and manage workloads effectively.
For technical leaders, the session offered a framework for assessing platforms and planning migration steps. For financial and administrative leaders, it offered a clearer understanding of the cost implications and governance questions that should guide the decision. The most valuable outcome was a clearer starting point: which questions to ask, which stakeholders to involve, and which risks need to be evaluated before the firm chooses a path.
For firms navigating VMware renewal pressures, there can be a strong temptation to act quickly. But the better approach is to step back, assess the environment, involve the right stakeholders, and build a decision framework that reflects the firm’s actual business, risk, and technology needs.
In the post-Broadcom VMware landscape, the real question is not whether firms will need to respond. It is whether they will treat that pressure as a forced migration or use it as an opportunity to build a stronger, more flexible infrastructure strategy.
Continue the Conversations after ILTACON 2026
Visit Kraft Kennedy’s ILTACON 2026 event page for post-conference updates and additional resources from the Kraft Kennedy team.