The backend's CSS was written “mobile first”, which means it starts with basic general styles and assigns all styles needed for bigger screen resolutions though media queries. I.e. the styles for smartphones in portrait orientation are inside
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@media only screen and (min-width: 480px) {}
However, in s9y's case, the style.css is not referenced “directly” in the <head> but through {$head_link_stylesheet}, which as far as I understand it means, it's piped through serendipity.css.php to include styles inserted via the css_backend hook.
Now, we could just reference a static IE8 stylesheet in a conditional comment, but that wouldn't include those styles inserted via serendipity.css.php, right? I'm not sure if that's even used in the current backend for backend styles. Doesn't look like it. But it might become an issue …
YL