June 24th, 2025 | 1:00PM ET / 10:00AM PT

Managing End-of-Life Systems Strategically

Prepare for Windows 10 and Beyond

You Don't Want to Hear This...

But your end-of-life systems are a ticking time bomb. With Windows 10 support ending in October 2025, millions of organizations are sitting on a cybersecurity powder keg. End-of-life systems don't just stop working—they become entry points for attackers, compliance nightmares, and budget disasters waiting to happen.

The WannaCry ransomware attack that crippled hospitals, railways, and businesses worldwide? It specifically targeted end-of-life Windows systems. Today, your Windows 10 machines are approaching that same vulnerable state, and the clock is ticking louder than most IT leaders realize.

Join our expert panel to discover how to identify EOL risks in your environment, choose an effective migration path, and transform what feels like an overwhelming deadline into an opportunity for strategic transformation.

What You'll Get From this Session:

  • Identify End-of-Life Risks: Learn systematic approaches to audit your systems and discover EOL vulnerabilities that may be hiding. Plus, understand security and compliance implications. 
  • Understand Your Windows 10 Migration Options: Get clarity on the different paths available for Windows 10 EOL, from direct upgrades to hardware refresh strategies, and how to plan your timeline effectively.
  • Develop Risk-Based Decision Making: Discover the key criteria for deciding when to replace versus secure end-of-life systems and how to evaluate business impact against security risks.
  • Contingency Planning: Learn specific compensating controls and security measures you can apply to EOL systems that can't be immediately replaced due to budget or operational constraints. 
  • Build Your EOL Planning Framework: Walk away with practical approaches to system inventory, application compatibility analysis, and essential steps for preparing your organization for future EOL transitions. 

Join us to learn how you can transform end-of-life challenges into manageable, strategic initiatives you can start implementing the right way.

From Tech Debt to Tech Fresh:

This session is ideal for organizations planning their first steps into the cloud or looking to expand their Azure footprint with new workloads while avoiding common pitfalls.

The workshop is particularly valuable for organizations that:

  • Are running Windows 10 systems with the October 2025 end-of-life deadline approaching
  • Have discovered end-of-life or unsupported systems during recent security assessments or audits
  • Are facing budget constraints that make immediate system replacement challenging
  • Need to maintain regulatory compliance while managing legacy technology infrastructure
  • Have experienced security incidents or near-misses related to outdated systems
  • Are struggling to inventory and assess the full scope of EOL risks in their environment
  • Want to develop proactive strategies rather than reactive crisis management for system lifecycles

Who Should Attend?

  • IT Directors and Managers  responsible for infrastructure planning and budget allocation who need strategic frameworks for addressing EOL systems across their entire technology stack.
  • System Administrators and Engineers tasked with maintaining legacy systems who require practical migration strategies and security hardening techniques for EOL environments.
  • Cybersecurity Professionals who need to assess EOL-related vulnerabilities and implement compensating controls to protect their organizations.
  • Compliance Officers and Risk Managers responsible for regulatory compliance who must understand how EOL systems impact audit requirements and risk assessments.
  • CISOs and IT Security Leaders who need to communicate EOL risks to leadership and develop comprehensive security strategies around aging infrastructure.
Our Expert Panel:

Hear from Our Experienced Cloud Experts

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Brendan Thompson

Director, Project Architecture and Delivery, Dataprise

Brendan Thompson is the Director of Project Architecture & Delivery at Dataprise, where he leads complex IT modernization initiatives. With deep expertise in managing end-of-life systems, Brendan helps organizations strategically retire legacy technologies while minimizing risk and ensuring continuity.

Joshua McNulty

Virtual Chief Information Security Officer, Dataprise

Joshua McNulty is a Virtual Chief Information Security Officer at Dataprise, specializing in end-of-life planning for IT systems. With a strong background from Drexel University and over a decade in cybersecurity leadership, Joshua excels in developing strategic decommissioning frameworks that reduce risk, ensure compliance, and support smooth transitions.