Add whitespace around image being cropped?

[jmancherje]

I have a circular image cropper for logos. Some people are complaining because they can't fit their logos into the circular cropper because it doesn't go beyond the bounds of the image. Here is a contrived example.

In this image you can see on the left, the logo is being cut off because the source doesn't have enough white space. Is it possible to add whitespace around an image so the circular cropper can have enough space to fit more of the image?

The image on the right is what I would like to do without requesting people create a new image manually and try again.