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It does not work when using the option overwrite existing files in version 2.1.0 on Umbraco 220.127.116.11.
I can't remember if it's based on physical file name, or the name of the media item, but have you made sure the names are exactly the same?
Other than that, I'd have to set it up and test, though it would be a little suprising for this issue to only pop up now, so hopefully it's down to some other issue.
In this case, the physical files had identical names. Byt the name of the media item where different.
The files I wanted to be overwritten was uploaded with a previous version of DMU, and then the names also had the file extension.
The new files where uploaded with the newest DMU, and in that one you have removed the file extensions to the media names.
I will do some more testing and get back to you.
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