Every year, Microsoft retires a new wave of products as it accelerates its cloud-first and AI-powered roadmap. For IT leaders, these changes can directly impact security, budget planning, operational continuity, and the ability to adopt the latest Microsoft innovations.
2026, in particular, is a year of major inflection points. Several widely deployed Microsoft platforms move into final support phases or are superseded by modern cloud equivalents. At the same time, Microsoft is combining parts of its security ecosystem. Most notably unifying Sentinel (SIEM) and Defender XDR–led operations under a single operational model.
This guide highlights the key product changes coming in 2026, so that you can prepare for how these may affect your organisation.
Why Microsoft End of Life in 2026 Matters for IT Leaders
End of Support isn’t just a date in a spreadsheet. It has real-world implications:
1. An increase in security risk
Unsupported systems become immediate targets for attackers. No patches, no fixes mean just vulnerabilities waiting to be exploited. In today’s landscape, this is no longer acceptable risk; it is a board level issue.
2. Blockers to modernisation and AI adoption
Legacy operating systems and server platforms cannot support Microsoft’s modern technologies such as AI services like Copilot. Staying on outdated systems means you cannot use the capabilities Microsoft is investing in the most. Therefore, limiting the innovation of your organisation.
3. Rising operational cost and technical debt
Legacy infrastructure becomes increasingly expensive to maintain, whether due to bolt on security solutions, extended support costs, or complex workarounds needed to keep ageing apps running.
2026’s Most Impactful End of Support Milestones
Mark your calendars. These are the product changes you need to know.
Windows 10
Deadline: 2026 marks the end of Year 1 ESU
While the primary Windows 10 end of support (EOS) date landed in 2025, many organisations will rely on Extended Security Updates (ESUs) through 2026. Crucially, 2026 is Year 1 of ESU, which is the lowest cost year before fees escalate significantly.
Remaining on Windows 10 means organisations shoulder increasing risk and cost. It also limits access to new capabilities delivered only on Windows 11, including Copilot and Intune management features.
For IT leaders, 2026 is the final window to:
- Complete fleet migration to Windows 11
- Retire non-compliant hardware
- Evaluate Windows 365 for legacy application continuity
- Refresh endpoint standards and Zero Trust policy enforcement
Windows Server 2016
Deadline: EOS 12 January 2027. 2026 is the final full year to migrate
Windows Server 2016 moves into its last full year of support in 2026, ahead of its hard EOS on January 12, 2027. Despite its age, it remains heavily deployed across midmarket and enterprise environments, often underpinning identity, file services, and key business applications.
Outdated servers introduce material risk into the environment. Particularly when used for Domain Controllers or critical application workloads. As a result, 2026 becomes the decisive year for planning and executing migrations.
Recommended priorities include:
- Assessing which workloads can be rehosted or modernised in Azure
- Upgrading or redesigning domain controller architecture
- Planning dependency remediation for older line of business apps
SQL Server 2016
Deadline: EOL on July 14, 2026
SQL Server 2016 remains common across operational reporting systems, ERP backends, and custom applications. Its hard deadline of 14 July 2026 means organisations must accelerate planning now, particularly where refactoring or cloud migration is required.
Migrating from SQL 2016 opens the door to:
- Azure SQL Managed Instance
- Azure SQL Database PaaS
- SQL Server 2022 (for on-prem regulatory or isolation requirements)
- A more modern data platform aligned to Azure, Fabric, and AI initiatives
SharePoint Server 2016
Deadline: EOL on July 14, 2026
On premises SharePoint is still widely used in organisations with complex intranet structures, document retention requirements, or customised workflows. These organisations face rising operational risk if they are not quick to react.
Migrating to Microsoft 365 brings significant benefits. Including more secure collaboration, modern intranet capabilities via Viva Connections, Power Platform based workflow automation, and reduced infrastructure overhead.
Office LTSC 2021
Deadline: EOL on October 13, 2026
This is important for organisations that deliberately avoided cloud subscriptions. Office LTSC 2021 was often purchased as the “safe”, perpetual alternative to Microsoft 365. But its end of support on 13 October 2026 forces a strategic decision:
- Move to Microsoft 365 Apps for Enterprise
- Or accept major compatibility, security, and integration limitations
More importantly, Office LTSC will not benefit from the rapid innovation cycle. Meaning your organisation will miss out on the latest AI and collaboration offerings that are central to Microsoft’s ecosystem.
Security Modernisation: Sentinel to Defender Portal Consolidation
This isn’t a product retirement, but it is a major operational shift.
New sunset date: 31 March 2027
Microsoft has extended the retirement date of the classic Log Analytics based Sentinel portal in favour of the unified Defender security portal, from 1 July 2026 to 31 March 2027. This allows customers to additional time to seamlessly migrate.
This change means:
- Investigation, hunting, and response become Defender centric
- Sentinel continues as a SIEM, but its UI moves into Defender
- SOC teams must retrain on new workflows
- Tooling consolidation may reduce duplicated platforms
This aligns with Microsoft’s broader strategy: unified SIEM and XDR experiences under Defender, reducing complexity and improving correlation across identity, endpoint, network, and cloud workloads.
Conclusion: 2026 Is the Year to Reduce Risk and Remove Roadblocks
The Microsoft products hitting end of support, or undergoing major strategic repositioning in 2026 represent some of the most widely deployed technologies in corporate IT.
Addressing them means reducing security risk, unlocking AI capabilities, and freeing your organisation from legacy technical debt.
Acting on these changes in 2026 will set the foundation for a more innovative future for your organisation.
Not sure where to begin? Reach out to one of our experts using the form below. Tell us the technology you are concerned about and we will be in touch to discuss a solution right for you.
