When we define @font-face styles, we can define whether the referenced files are for the bold, italic, or bold italic versions of a font, as discussed in this SO question:
It does involve poking around inside the font to determine when a font is bold or italic. And certain bits must be set inside the font in order for IE to pick up the style linking. Most bold / italic fonts have these bits set, but not all. We are working on a way to make this more automatic.