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Uninstall & Reinstall Issues

How to Replace Office 2016 with Microsoft 365 on an iMac Without Losing Files

John WilsonJohn Wilson Oct 16, 2026 869 views

Question details

The user wants to upgrade from Office Home & Student 2016 to Microsoft 365 Personal on a Mac without deleting existing documents.

How to Replace Office 2016 with Microsoft 365 on an iMac
Product
Microsoft Office
Device & OS
macOS (iMac)
Scenario
Upgrading Microsoft Office applications from a one-time purchase version to a subscription version on an iMac.
Observed behavior
Needs to cleanly remove the old software and install the new version while ensuring personal .docx and .xlsx files remain intact.
Before you start

Ensure you have the login credentials for the Microsoft account associated with your new Microsoft 365 Personal subscription before removing your old software.

Solution 1Recommended

Uninstall Office 2016 and Install Microsoft 365

Remove the outdated Office applications and supporting files, then download the new installer directly from your Microsoft account.

Uninstalling Microsoft Office applications from your Mac will not delete your personal documents, spreadsheets, or presentations. Your files are stored separately from the application files and will seamlessly open in Microsoft 365 once the installation is complete.

1
Remove Office 2016 Applications

Open Finder, navigate to the Applications folder, and drag all Microsoft Office 2016 apps (Word, Excel, PowerPoint, Outlook) to the Trash.

2
Clean Up Support Files

Open Finder, press Command+Shift+G, and type '~/Library' to access the hidden Library folder. Locate and remove Microsoft-related support files found in the 'Containers' and 'Group Containers' folders.

3
Clear Old License Data

Download and run the Microsoft Office license removal tool to clear any remaining Office 2016 activation files from your Mac. This prevents conflicts with your new Microsoft 365 subscription.

4
Download Microsoft 365

Open your web browser, navigate to www.office.com, and sign in using the Microsoft account linked to your Microsoft 365 Personal subscription. Click the 'Install Office' button.

5
Install and Activate

Locate the downloaded installer package in your Downloads folder. Double-click to run it, follow the on-screen prompts to complete the installation, and launch Word to verify your activation.

Uninstall Office 2016 and Install Microsoft 365
Document Safety Assured: All your existing .docx and .xlsx files will automatically associate with the newly installed Microsoft 365 applications.
Free Microsoft Office alternative

Upgrade Your Mac Productivity with WPS Office

Looking for a hassle-free and affordable upgrade? WPS Office is a lightweight, all-in-one suite that perfectly supports Microsoft formats without requiring expensive subscriptions or complicated uninstallation processes.

  1. 1. Download for Mac: Visit the WPS Office website and download the Mac version of the software.
  2. 2. Install Quickly: Open the downloaded package and drag the WPS Office icon into your Applications folder.
  3. 3. Open Existing Files: Launch WPS Office and instantly open your old Word and Excel documents without compatibility issues.
Seamless compatibility with Microsoft Office formats (.docx, .xlsx, .pptx)Lightweight app that installs quickly and saves storage on your iMacAll-in-one tabbed interface for managing documents, spreadsheets, and PDFs simultaneouslyFree to use with a familiar user interface for a smooth transition
microsoft office alternative - wps office

Frequently Asked Questions

Will uninstalling Office 2016 delete my Word documents?

No, uninstalling Microsoft Office only removes the application files from your system. Your personal files, including Word documents (.docx) and Excel spreadsheets (.xlsx), remain safely stored on your Mac's hard drive.

Do I need to use the Microsoft license removal tool on my iMac?

Yes, running the license removal tool is highly recommended when upgrading from a one-time purchase like Office 2016 to a Microsoft 365 subscription. It clears old activation data that might otherwise cause the new apps to fail activation.

Can I run both Office 2016 and Microsoft 365 on the same iMac?

Microsoft does not recommend having multiple versions of Office installed on the same Mac, as it often leads to software conflicts, document association errors, and activation issues. You should completely uninstall the older version before installing Microsoft 365.