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  1. As already mentioned, Regenerate Thumbnails plugin triggers the (re)generation of image sizes which are currently defined via add_image_size() or similar.

    Here is a patch to modify Regenerate Thumbnails Version 2.2.0 so it will delete any previously generated image-sizes, including older outdated sizes before creating the new sizes.

    http://wordpress.org/support/topic/how-to-delete-old-thumbnail-images

    Important: Note that URLs to images are hard-coded in posts and pages. Removing old thumbnails could result in broken images if they are still used somewhere on your site. You have been warned…