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Fix SharePoint Not Showing Replace or Keep Both for Duplicate Files
Question details
Users are unable to select the 'Replace' or 'Keep Both' options when uploading duplicate files to SharePoint, as the system automatically changes the file name instead.
- Product
- Microsoft SharePoint
- Device & OS
- not provided
- Scenario
- Uploading a file into a SharePoint document library where a file with the exact same name already exists.
- Observed behavior
- The expected 'Replace or Keep Both' prompt does not appear. Instead, the newly uploaded file is automatically renamed by appending a number, even when library versioning is enabled.
Verify that versioning is fully enabled in your SharePoint document library settings, and confirm whether you have Microsoft 365 administrative privileges to request tenant-level configuration reviews.
Contact Microsoft Support for Tenant Behavior Changes
Address the new SharePoint update that automatically appends numbers to duplicate files by having an administrator open a support ticket.
Microsoft frequently rolls out behavior changes at the tenant level for Microsoft 365 environments. A recent rollout changes the default duplicate file handling from displaying a 'Replace or Keep Both' prompt to automatically appending a number to the duplicated filename.
Because this setting is enforced at the tenant level, standard users and site owners cannot revert this behavior through the standard SharePoint interface. A Microsoft 365 administrator must review the tenant settings and contact Microsoft Support directly.
Sign in to the Microsoft 365 Admin Center using an account with administrator permissions.
Locate and click on the 'Support' section in the left-hand navigation menu, then select 'Help & support'.
In the search pane, type a brief description of your issue, such as 'SharePoint duplicate file prompt missing', and press Enter to search for relevant tenant advisories.
If the provided self-help articles do not resolve or explain your specific tenant's behavior, click 'Contact support' to open a ticket with Microsoft regarding the automated file renaming rollout.
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Frequently Asked Questions
Why did SharePoint stop asking me to replace files?
Microsoft has implemented a tenant-level update that automatically appends a number to duplicate files during upload. This is designed to prevent accidental data overwriting but bypasses the traditional 'Replace or Keep Both' prompt.
Can I fix the duplicate file behavior without admin rights?
No. Since this behavior is controlled by tenant-level settings rolled out by Microsoft, standard users do not have the permissions to change it. You must contact your organization's IT administrator.
Does enabling versioning bring the prompt back?
Not necessarily. Users report that the prompt remains hidden and files are auto-renamed even when document library versioning is fully enabled, confirming the change is tied to a wider tenant update rather than local library configurations.
How can I intentionally replace a file if the prompt is missing?
As a workaround, you can manually delete the existing file in SharePoint before uploading the new one. Alternatively, open the existing document in your browser or desktop app and copy-paste the new content into it to create a new version.
