On October 14, 2025, Microsoft ends support for multiple critical products simultaneously. This date represents one of the most significant technology transitions in recent years, affecting millions of organisations worldwide.
Microsoft's end-of-support date affects a comprehensive range of business-critical applications.
This collective retirement creates an unprecedented challenge for IT departments, Service Providers and Consultants tasked with managing integrated Microsoft environments.
In short, Yes.
After October 14, 2025, affected products will no longer receive security patches, bug fixes, or technical support from Microsoft. This creates POTENTIAL immediate vulnerabilities that cybercriminals can exploit, knowing these flaws will never be patched. Recent zero-day vulnerabilities discovered in Office 2016 demonstrate that this is a clear and ongoing security risk.
Organisations continuing to use such unsupported software WILL face exposure to malware, ransomware and the associated data breaches. Each unpatched vulnerability becomes a permanent entry point for attackers.
Compliance frameworks like ISO 27001 and the ACSC Essential Eight as well as privacy regulations increasingly require organisations to maintain supported software - choosing to ignore the Microsoft "End of Support" date is the same as choosing to ignore compliance regulations - plain and simple.
Beyond the clear security concerns, organisations will face significant and ever increasing operational disruptions. As an example, since Microsoft 365 integration support with older Office versions was discontinued in 2023, many users have experienced the impact of no email in Outlook and having to revert to Webmail access.
Line-of-business applications that integrate with Office products will experience similar failures. ERP systems, CRM platforms, and financial applications often rely on Excel integration or (Legacy!) Outlook plugins for critical workflows. As these older Office versions fall further behind cloud service standards, essential business processes will break without warning and cause un-planned impacts on significant portions of your workforce.
The simultaneous retirement of Windows 10 and Office compounds these compatibility issues - some new Windows 11 features and security protocols may not work properly with legacy Office installations, forcing organisations into reactive troubleshooting rather than planned transitions (and the frustration and diversion from critical projects that this causes).
Lets be really Clear:
The cost of inaction far exceeds the investment in planned upgrades.
For Windows 10 Extended Security Updates, business pricing starts at US$61 per device for the first year, doubling to US$122 in year two, and reaching US$244 in year three - that's a total of US$427 per device over three years! While this WILL give you access to CRITICAL security upgrades, it WON'T protect you from software compatibility issues or extend the life of older office applications.
Migration costs to Microsoft 365 typically cost between $50 & $250 per user depending on complexity and mailbox count. While this is a substantial upfront cost, these investments provide long-term value through improved security, collaboration capabilities, and reduced maintenance overhead. Delaying this will increase the chance of needing to do an emergency migration, with costs that are likely some 40-60% higher due to compressed timelines, limited planning options and increased risk of unforeseen impacts!
The hidden costs of remaining on unsupported software include increased IT support time, potential compliance fines, cyber insurance premium increases, and business disruption from security incidents. A single ransomware attack can cost organisations hundreds of thousands of dollars in recovery efforts, legal fees, and lost productivity.
Small organisations (under 50 users) prioritise immediate assessment and pilot testing. Begin with a small group of users to validate new software compatibility with existing workflows. Microsoft 365 Business Basic provides cloud-based Office applications with essential security updates. Consider simultaneous Windows 11 upgrades to maximise compatibility and minimise disruption.
Medium organisations (50-250 users) require phased deployment strategies. Start with pilot groups in less critical departments while maintaining parallel systems during transition. Microsoft 365 Business Premium includes advanced security features essential for growing businesses. Plan for 3-6 month migration timelines to allow proper testing and training.
Large organisations (250+ users) need comprehensive enterprise planning. Leverage Microsoft FastTrack services for eligible subscriptions and consider Microsoft 365 E3 or E5 licensing for advanced compliance and security features. Implement staged rollouts by department or location, maintaining detailed compatibility testing for line-of-business applications. Budget for extensive change management and user training programmes.
Organisations have three primary upgrade paths:
Microsoft first announced the October 14 2025 deadline back in June 2022, to give users ample time to prepare for the end of support and transition to a more supported operating system.
For those with their heads buried in the sand, there is STILL TIME to effectively handle this. Here are our top three tips to prepare for the fast-approaching deadline.
Successful transitions require proactive risk management.
The complexity of simultaneous Windows and Office transitions often exceeds internal IT capabilities. Engaging experienced migration specialists can prevent costly mistakes and ensure smooth transitions. Professional services typically include compatibility assessment, migration planning, user training, and post-deployment support.
Choose partners with demonstrated Microsoft expertise and references from similar organisations. Avoid providers offering unusually low prices without comprehensive service inclusion. Successful migrations require thorough planning, testing, and change management support.
The October 14, 2025 deadline represents a critical inflection point for organisational technology strategy. Proactive planning and early implementation will ensure smooth transitions while maintaining business continuity and security. Organisations that delay face increasing costs, security risks, and operational disruptions that could have been avoided through timely action.