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Many companies, including some of the UK’s largest banks, major retailers, and government departments, are still grappling with the fallout from legacy software. Compatibility issues and security risks tied to aging platforms remain widespread. This familiar pattern means migration projects are often postponed until the last minute, increasing the risk of costly disruptions and avoidable security vulnerabilities.Microsoft’s decision to end support for Microsoft Teams Classic on 1st July is more than just a routine update deadline; it represents a critical juncture for enterprise IT teams. For many organizations, this is a firm cutoff with serious operational and security implications.Stopgap measures bring their own challengesThe impact of these delays is already evident. Many enterprises are paying for Extended Security Updates (ESUs) to buy extra time, while others are accelerating hardware refresh cycles, replacing laptops and desktops earlier than planned just to keep pace. Yet these stopgap measures bring their own challenges. Rushed rollouts often trigger user frustration, operational hiccups, and technical setbacks, complicating what should be a straightforward upgrade.Security concerns are particularly acute. Recent breaches at major UK retailers such as Marks & Spencer and the Co-op were directly linked to weaknesses in legacy systems. These incidents underline a stark reality that running unsupported software is a liability that can have serious consequences for both security and reputation.Windows 10 complicationsThe October deadline for Windows 10 support compounds the challenge. While Microsoft will continue offering paid ESUs for Windows 10, these only provide a temporary patch rather than a long-term solution. Organizations relying on extended support risk developing a false sense of security. Without a full platform upgrade, vulnerabilities pile up, documentation becomes obsolete, and the loss of staff familiar with legacy systems makes future migrations more complex and expensive.For IT teams facing the double challenge of migrating both Teams and Windows 10 within months, the situation is stressful. Budgets are tight, resources limited, and the window to complete a compliant and smooth transition is rapidly closing.Often, delaying migration comes down to competing priorities, constrained budgets, and a lack of clear understanding about how legacy systems interact with current business processes. Legacy environments are typically poorly documented, and over time, institutional knowledge is lost as experienced staff leave. This makes migration projects time-consuming and costly, not only in terms of software upgrades but also in mapping the impact on security and compliance.Postponing these migrations carries hidden costs too. Every month that passes increases the risk of security breaches, operational failures, and regulatory penalties. Delaying upgrades becomes an increasingly risky gamble.Successfully navigating this challenge Successfully navigating this challenge demands urgent action and careful planning. One lesson from past migrations is clear in that scheduling rollouts thoughtfully and having robust rollback alternatives in place are crucial to minimize disruption. The old adage “plan for success but prepare for failure” rings especially true here. Working closely with users throughout the process helps manage expectations and surface issues early on.Another key priority is capturing institutional knowledge before critical staff move on. Documenting legacy configurations, workflows, and vendor agreements is vital to maintain continuity and enable effective troubleshooting during migration. Testing compatibility thoroughly in controlled environments is also crucial to spot potential problems before they affect users. Planning phased rollouts with clear fallback procedures helps manage risk and keeps disruptions to a minimum.At the same time, clear communication and user training can’t be overlooked. Engaging with end users early reduces resistance and confusion, helping teams adapt smoothly to the new platform without unnecessary setbacks.End of supportThe end of Teams Classic support should serve as a clear warning that last-minute fixes and reliance on extended support aren’t sustainable. In an era where digital transformation and cyber threats are accelerating, organizations need to take control of their technology lifecycles. Early, comprehensive planning combined with cross-team collaboration is the only way to ensure timely migration while maintaining security and operational stability.Those organizations that act now will not only meet critical deadlines but will also reduce risks and build resilience for the future. For those that continue to delay, the risks of costly disruptions, breaches, and compliance failures will only grow.With time running out on both Teams Classic and Windows 10 support, the path forward requires decisive, well-coordinated action to safeguard security and prepare organizations for the challenges ahead.We've compiled a list of the best patch management software.This article was produced as part of TechRadarPro's Expert Insights channel where we feature the best and brightest minds in the technology industry today. The views expressed here are those of the author and are not necessarily those of TechRadarPro or Future plc. 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