If your organization still runs Office 2016 or Office 2019, you’re up against a hard deadline. Microsoft will end support on October 14, 2025, which means no more security updates, bug fixes, or tech support. The apps won’t suddenly stop working, but the security and compliance risks climb quickly. The good news: there’s a practical lifeline if you can’t—or don’t want to—move to Microsoft 365 yet.
WHAT HAPPENS ON OCTOBER 14, 2025
Microsoft ends support for Office 2016 and Office 2019 on October 14, 2025. Word, Excel, PowerPoint, Outlook, and related components continue to run, but they stop receiving security and reliability patches. That lack of updates leaves devices more exposed, can break compliance baselines, and complicates support from vendors and MSPs.
For many shops, this date lands alongside other Microsoft milestones. Windows 10 also exits support on the same day, and older server workloads like Exchange Server 2016 and 2019 hit end-of-life timelines. Taken together, October becomes a change window you can’t ignore.
WHY STAYING PUT IS RISKY
Unsupported Office clients become a weak link. Attackers watch for unpatched software because new vulnerabilities are often discovered—and quietly exploited—after support ends. That’s especially true for widely deployed apps that process untrusted content daily, like email attachments and spreadsheets.
Beyond security, compatibility erodes. New file format features, add-ins, cloud integrations, and modern authentication patterns target supported Office builds first. Over time, users see odd behavior: templates fail, macros break, meeting add-ins misbehave, and collaboration with Microsoft 365 tenants becomes painful.
[TIP] If you must keep a legacy workstation for a niche tool, isolate it with strict network controls and use it only for that purpose.
YOUR UPGRADE PATHS
Microsoft 365 (subscription) and Office LTSC 2024 (perpetual) are the two realistic destinations. The right choice depends on your connectivity, regulatory posture, budget model, and change tolerance.
Microsoft 365 (subscription)
The cloud-first track delivers the most features and the fastest fixes. You get current apps, real-time collaboration, modern security baselines, and access to emerging AI experiences.
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Continuous security and feature updates
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Best path for hybrid and remote work
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Simplifies add-in and integration support
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Predictable per-user, per-month costs
Office LTSC 2024 (perpetual)
LTSC (Long-Term Servicing Channel) is built for devices that can’t accept frequent feature changes or live off the internet. It’s a fixed feature set with security updates during its lifecycle.
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Perpetual licensing for specific scenarios
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No real-time collaboration or rapid feature cadence
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Familiar deployment tools for IT (Click-to-Run, KMS/MAK)
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Useful for lab instruments, control systems, kiosks, VDI images
Who Should Choose What
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Pick Microsoft 365 if you need collaboration, coauthoring, Teams/Outlook add-in harmony, and the newest security controls.
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Choose Office LTSC 2024 for air-gapped, compliance-locked, or tightly managed endpoints that can’t handle frequent changes.
WHAT TO KNOW ABOUT OFFICE LTSC 2024
Office LTSC 2024 replaces older perpetual suites for commercial customers who require on-premises Office. It shifts legacy MSI installs to Click-to-Run technology, but activation and policy management (KMS/MAK, Group Policy) remain familiar. Add-ins that worked on Office 2019 and LTSC 2021 typically need only light testing.
Practical notes for deployment:
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Plan to remove legacy Office during install; LTSC can handle removal as part of setup.
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Lock your build and update rings to align with your change-control cadence.
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Validate macros, COM add-ins, and line-of-business integrations in a pilot first.
[NOTE] LTSC 2024 offers a stable feature set by design. If your stakeholders expect fast-moving features—or Copilot experiences—go with Microsoft 365 Apps.
WINDOWS 10, EXCHANGE, AND SKYPE: THE PARALLEL DEADLINES
October 14, 2025 is a cluster of end-of-support events. Windows 10 exits support that day, and many organizations will weigh extended security options versus accelerating PC refreshes or Windows 11 upgrades. Exchange Server 2016 and 2019 also reach their end-of-life timeline, which pushes email shops to plan migrations to Exchange Online or newer server editions. If you’re still on Skype for Business, it’s another nudge toward Teams.
Treat this as a coordinated portfolio change, not a one-off Office swap. Aligning endpoints, identity, and messaging upgrades reduces rework and limits migration fatigue across your user base.
HOW TO PLAN THE MOVE (CHECKLIST)
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Inventory Reality
Build a hardware and software inventory. Identify who is on Office 2016/2019, which add-ins they run, and which documents rely on macros or legacy templates. -
Choose a Track
Decide between Microsoft 365 and Office LTSC 2024 per persona or device class. Many organizations land on a mixed model: M365 for knowledge workers, LTSC for specialized stations. -
Pilot and Test
Create a pilot ring with power users from each department. Validate macros, add-ins, label/sensitivity policies, and meeting add-ins. Capture any file format or font regressions early. -
Address Dependencies
Check identity and security baselines: modern auth, Conditional Access, and data loss prevention. If you’re moving mail, line up Exchange and Outlook profile changes with the Office rollout. -
Communicate and Train
Publish “what’s changing” guides that focus on daily workflows. Keep training short and contextual: 15-minute videos, quick-start PDFs, and department-specific tips. -
Deploy in Waves
Automate install and removal with your management stack (Intune, ConfigMgr, or your RMM). Use rings: pilot → early adopters → broad rollout. Monitor crash reports and help desk trends. -
Contain the Legacy
For devices that must stay on old Office temporarily, enforce network segmentation, remove local admin rights, and block internet access where feasible. Document an exit date.
Quick Wins to Reduce Friction
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Pre-stage templates, fonts, and add-ins in the new build
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Standardize ribbon customizations via policy
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Map old shortcuts to new equivalents in a one-pager
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Provide a self-service “Fix my Office” script for common issues
COST AND LICENSING CONSIDERATIONS
Budgeting differs by path. Microsoft 365 is OPEX-friendly with per-user pricing and bundles that can offset other tool costs (security, storage, collaboration). LTSC 2024 is CAPEX-like and often licensed per device, which fits labs and shared endpoints. Whichever route you choose, factor in help desk load, user training, and the opportunity cost of staying on unsupported software.
A measured plan beats a last-minute scramble. Treat October 14, 2025 as a forcing function to modernize where it makes sense, and to stabilize where it doesn’t. If you need continuity without the cloud, Office LTSC 2024 is a viable, supportable bridge; if you want collaboration velocity and the newest capabilities, Microsoft 365 is the clear destination.
If this was helpful, share it with your team and drop your questions or lessons learned in the comments—I’ll add FAQs and deployment tips in future posts.
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