Oof. I think that's this issue: http://stackoverflow.com/questions/5069752/ios-4-2-webfont-ttf-s-bold-font-weight-rendering-bug http://stackoverflow.com/questio

Oof. I think that's this issue: http://stackoverflow.com/questions/5069752/ios-4-2-webfont-ttf-s-bold-font-weight-rendering-bug http://stackoverflow.com/questions/5069752/ios-4-2-webfont-t... I think the problem is that none of the TTFs include bold italic, so the browser generates a 'fake bold' of the italic. This time, MobileSafari is doing it oddly. Apparently a workaround is to fake bold yourself with -webkit-text-stroke (icky) and pretty workarounds would be to avoid bold italic or have a separate .ttf for it.