Upload a New Version of a File
Upload a new version of a file without checking out the existing file.
Go to the item for which you want to update an attached file.
On the Attachments tab, select the file that you want to update.
Click ... and select Upload New Version.
Select the file to upload and click Open.
Enter a description for the file.
Click Upload.
The upload progress is shown at the top of the screen. When it finishes, the version number for the file increases by one.