Currently the file page provides a set of different image sizes for the user to directly access. These sizes are usually width-based. However, for tall images they are height-based. The thumbnail urls, which are used to generate them pass only a width.
What this means is that tall images end up with arbitrary thumbnail widths that don't follow the set of sizes meant for the file page. The end result from an ops perspective is that we end up with very diverse widths for thumbnails. Not a problem in itself, but the exposure of these random-ish widths on the file page means that we can't set a different caching policy for non-standard widths without affecting the images linked from the file page.
I see two solutions to this problem, if we want to introduce different caching tiers for thumbnail sizes that come from mediawiki and thumbnail sizes that were requested by other things.