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I was really excited to see the new functionality with the media manager in WP 3.3 (specifically drag and drop uploads and automatic file type recognition)

But I was disheartened to see no relief in terms of the confusing manner in which WP continues to handle image overwrites (by appending a number to the image and creating a duplicate version).

Does anyone have a workaround that I can implement in my theme's functions.php to enable automatic image overwrites, replacing the original image with the new one, and without changing the filename?

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There's another plugin out there worth checking out:

Enable Media Replace
This plugin allows you to replace a file in your media library by uploading a new file in its place. No more deleting, renaming and re-uploading files!

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Some searching revealed a plugin that seems to work, Overwrite Uploads. However, this requires a small change to the wp core, which isn't great. So far I haven't found any way around this.

On a sidenote, I've used WPlupload to replace the built in uploader. I like how it lets me set a max upload file size and resolution. not sure if it helps with your problem but might be useful to check out.

By the way, this has been asked a few times before with the same suggestion.

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