Currently, it looks like the thumbnails are generated by fitting the width of the image and cropping the rest. The user should also be able to generate a thumbnail by fitting the height and fitting both the width and height. When you click Change Thumbnail, there should be a drop down menu with the following options in the Delete current thumbnail Box (since that's what regenerates it): Fit width Fit height Fit width and height It would also be nice to choose how it is generated when you first upload the image. Maybe it would be a setting for all of the currently uploaded images instead of individually (to save space). Here's an example of an image that looks bad with the current thumbnails. Image: Thumbnail: Edit: It would also be useful to set the default behavior. Edit 2: I'm thinking the setting should be saved with the media so that it will still work properly if the thumbnail gets regenerated later.