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Update & Upgrade Problems

How to Upgrade Outlook 2016 to Microsoft 365 Without Losing Data

Phi Hung VoPhi Hung Vo Oct 10, 2026 868 views

Question details

The user wants to upgrade their unreliable version of Outlook 2016 to Microsoft 365 and needs to ensure that email history, folders, rules, and profiles are safely preserved during the process.

How to Upgrade Outlook 2016 to Microsoft 365 Without Losing Data
Product
Microsoft Outlook
Device & OS
not provided
Scenario
Upgrading an older, perpetual license version of Outlook (2016) to the newer subscription-based Microsoft 365 version due to application crashes and unreliability.
Observed behavior
Outlook 2016 has become unreliable, occasionally failing to open or process links correctly. The user wishes to transition to Microsoft 365 without losing locally stored profile data.
Before you start

Before upgrading, verify that your current Outlook issues are not caused by a corrupted user profile, as a software upgrade will inherit the existing profile and may not resolve profile-specific errors.

Solution 1Recommended

Uninstall Office 2016 and Install Microsoft 365

Removing the older version of Office will not delete your Outlook profile data. The new Microsoft 365 installation will automatically reconnect to your existing emails, folders, and rules.

Microsoft 365 is a subscription service, whereas Office 2016 is a perpetual license. Installing Microsoft 365 does not automatically remove Office 2016, which can lead to application conflicts and unreliable behavior. You must manually uninstall the older version first.

1
Uninstall Office 2016

Open the Control Panel on your Windows computer, navigate to 'Programs and Features', locate your Microsoft Office 2016 installation in the list, right-click it, and select 'Uninstall'.

2
Install Microsoft 365

Log in to your Microsoft account at office.com, navigate to your account dashboard, and click 'Install Office' to download and run the Microsoft 365 installer.

3
Launch the New Outlook

Once the installation is complete, search for Outlook in your Start menu and open it. The application will automatically detect and load your existing Outlook profile, including your email history, folders, and rules.

Uninstall Office 2016 and Install Microsoft 365
Profile Preservation: Uninstalling Office normally does not remove the Outlook profile, which securely stores your account configuration and data-file information locally on your hard drive.
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Frequently Asked Questions

Will I lose my emails if I uninstall Outlook 2016?

No. Uninstalling the Outlook application only removes the software files. It leaves your Outlook profile, which contains your emails, rules, and account settings, completely intact on your system for the new version to use.

Why is my Outlook 2016 crashing even though I have a Microsoft 365 subscription?

Having multiple versions of Office installed or using an outdated perpetual license can cause file association conflicts and performance issues. Completely removing the old version and installing the Microsoft 365 version often resolves these software reliability issues.

How do I know if I'm currently using Outlook 2016 or Microsoft 365?

Open Outlook, click on the 'File' tab in the top left corner, and select 'Office Account' (or just 'Account'). Under the 'Product Information' section on the right, you will see exactly which version is currently active.

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

While it is technically possible in some scenarios, it is highly discouraged. Running both simultaneously usually leads to software conflicts, update errors, and application crashes. Always uninstall the older version first.