Force Regenerate Thumbnails allows you to delete all old images sizes and REALLY regenerate the thumbnails for your uploads.

Regenerate all thumbnails from the Tools admin menu. Regenerate batches of images via the Media Library list mode. Select the images to regenerate and then use the Bulk Actions drop-down menu to Force Regenerate Thumbnails. Use attachment actions to regenerate thumbnails for a single image.

Several filters exist for advanced usage. See more via this gist.

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