Hi @John Kanost ,
Thank you for posting in this community.
I tested this in my Sharepoint 2019 environment. As expected, ask if you need to replace the one that already exists.Click Replace, it will overwrite the original file with the new one.
It seems this is not a common issue per my test. However, we can work together to narrow down and resolve the situation. So, Please kindly provide more information below to let us work further.
1.Make sure your SharePoint Server is up-to-date with the latest patches and updates.
2.Sometimes browser compatibility can cause issues. Try using a different browser or ensure that your current browser is not in compatibility mode.
3.Try to Upload Using File Explorer:
- Open the SharePoint library in File Explorer (Windows Explorer).
- Navigate to the folder where you want to upload the new version of the document.
- Drag and drop the updated document from your local drive into the SharePoint library.
- SharePoint should handle the versioning and replacement automatically.
Hope the information can help you.
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