All in all, WordPress offers a pretty robust media manager. It's fairly simple to add…
When you upload an image to WordPress with the same filename as an already existing image, the file will be renamed so as not to override the current image. Overwrite Uploads bypasses this functionality so you can easily overwrite old images.
What’s It Do?
Overwrite Uploads will detect new uploads with the same file name of an uploaded image, delete the original, and then upload the new file, overwriting the original. So let’s say you have an image called “myimage.jpg” on your site. But you have an updated version of “myimage.jpg” you want to replace it. With this plugin, you simply upload your new version and it will delete the old version. By default in WordPress, you would have to manually delete the old version before uploading the new one.
For some people, this is desired functionality for replacing images or to keep the latest versions of images on your site. If this is something you need, you simply need to install the plugin.
How’s It Work
This plugin is one of those that you simply activate and it starts working. There are no settings for it, so new images will begin overwriting old images automatically. If you ever wish to turn this functionality off, all you have to do is deactivate the plugin.
Keep in mind, that only images uploaded in the same month will be overwritten. This is because of WordPress stores images in folders according to month (2014/1/, /2014/2/, etc.). If a file has the same name but lives in a different directory the overwrite function is not needed. Just something to keep in mind.
Costs, Caveats, Etc.
The plugin has been recently rewritten in order to make it more turnkey and easier to use. It works with the newest version of WordPress. If you are having any problems with the plugin, you can visit the support forums.