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Support for Office 2016 and Office 2019 ends on October 14, 2025. After that date, Microsoft will no longer provide updates or support, leaving these legacy versions vulnerable to security threats and compliance issues.
Now is the time to plan your upgrade to Microsoft 365.
Why You Must Migrate
No more security updates or vendor support after October 14, 2025
Increased risk of ransomware and malware without ongoing security updates
Compliance concerns in regulated industries without supported software
With these risks in mind, it's recommended to start transitioning away from Office 2016 and 2019 as soon as possible.
How Automox Supports Your Migration
Use Automox to:
Routinely scan for and detect legacy Office installations
Automatically uninstall Office 2016 and 2019
Deploy Microsoft 365 apps across devices
Monitor migration progress in real time
Automox works across Windows, macOS, and Linux. Automox Worklets™ are prebuilt automations in the platform that help with vulnerability remediation, configuration enforcement, auditing, and more.
Worklets to Streamline Your Migration
Windows - Software Lifecycle - Upgrade Microsoft Office (MSI) to Microsoft 365 Performs an in-place upgrade from legacy Microsoft Office (MSI) 2016–2019 installs to Microsoft 365 (Click-to-Run).
Download and Install Microsoft Office 365 Worklet for macOS – Bash script that downloads and installs Office 365 on macOS devices.
Office Click‑To‑Run Uninstaller Worklet – Uninstalls Office Click-to-Run versions, including 2016, 2019, and early Microsoft 365 builds.
These Worklets are prebuilt for you in the Automox Worklets Catalog.
Migration Checklist With Worklets
Option 1: In-Place Upgrade for Office 2016 / 2019 MSI Versions
1. Detect, uninstall, and upgrade legacy MSI-Office versions to M365
Grab the Upgrade Microsoft Office (MSI) to M365 Worklet from the Automox Worklet Catalog. Create a policy that runs weekly to automatically detect and upgrade legacy MSI-installed versions of Office 2016 and Office 2019 to M365.
2. Monitor progress
Track Office 365 deployment status across devices through the Policy Results Report.
3. Stagger deployment waves
Schedule deployments to minimize user disruption, prioritizing groups or business units starting with the lowest risk, and monitoring your policy success with the Policy Results Report.
Option 2: Uninstall & Reinstall for Office 2016 / 2019 Click-to-Run Versions
Detect and uninstall legacy Click-to-Run Office versions
Grab the detection and uninstall Worklet from the Automox Worklet Catalog. Create a policy that runs weekly to automatically detect and uninstall Click-to-Run versions of Office 2016 and Office 2019. This Worklet will detect legacy Click-to-Run versions of Office and uninstall them according to the schedule you set.
Protip: Monitor the Policy Results to see successful and failed runs to the device level.
Deploy Microsoft 365 apps
Use the Install M365 Apps Worklet on Windows, or the macOS Office 365 installation Worklet on Macs, to deploy the latest Office suite. An automated policy is recommended to ensure that end user productivity isn’t interrupted.Monitor progress
Track Office 365 deployment status across devices through the Policy Results Report.Stagger deployment in waves
Schedule deployments to minimize user disruption, prioritizing groups or business units starting with the lowest risk, and monitoring your policy success with the Policy Results Report.
Take Action Before Support Ends
Start migrating to Microsoft 365 now to avoid security risks and compliance gaps after October 14, 2025. With Automox Worklets, you can automate detection, uninstallation, and deployment — all with minimal user disruption.
Sources
Windows 10 End of Life - Another critical Microsoft migration with the same October 2025 deadline
Patch Management Best Practices - Best practices for managing software lifecycle and patching across your fleet
Top Ways to Manage Third-Party Patching - Office is one of many third-party applications that need consistent update management
Frequently asked questions
Microsoft ended support for Office 2016 and Office 2019 on October 14, 2025. After this date, these versions no longer receive security updates, bug fixes, or technical support, leaving organizations exposed to unpatched vulnerabilities.
The applications will continue to function, but they will no longer receive security patches. This means any newly discovered vulnerabilities will remain unpatched, creating compliance risks and increasing your attack surface. Many regulatory frameworks require running supported software.
Yes. Automox provides pre-built Worklets that handle detection of legacy Office installations, uninstallation of old versions, and deployment of Microsoft 365. The process supports both MSI-based in-place upgrades and Click-to-Run uninstall/reinstall scenarios across Windows and macOS.
The actual installation typically takes 15-30 minutes per device depending on network speed and hardware. With Automox, you can run the migration in the background during business hours or schedule it during maintenance windows. The full fleet migration timeline depends on your staged rollout plan.
No. Best practice is a phased rollout: start with a pilot group of 5-10% of devices, monitor for issues over 24-48 hours, then expand to broader groups. Automox policies let you target specific device groups and track progress through Policy Results Reports.