By my reading of the background-size spec, values that use keywords are not animatable.
https://drafts.csswg.org/css-backgrounds/#the-background-size
Animatable: as repeatable list of simple list of length, percentage, or calc (This means keyword values are not animatable.)
This means that you can't animate from background-size: 10px to background-size: 20px due to the implicit presence of the auto keyword (background-size: 10px computes to background-size: 10px auto).
Chrome <=50, Firefox, Safari and Edge will animate the above example, IE doesn't animate background-size.
Chrome 51 stopped animating these cases and received a bug report about it: http://crbug.com/616072
Chrome intends to revert its behaviour for compatibility with other browsers and animate background-size when keywords are positionally matched.