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SmartyPants - there may be some small issues that are causing your troubles:
1. sometimes the font is not able to be displayed properly by the sony reader. sometimes it is easier to try someone else's font that you know works and then substitute your own. one example of this is the font format ie ttf vs otf.
2. the css code needs to be perfect - any spelling errors and it won't work
3. often, calibre has problems overwriting the css of the original file, if so, then choose the tweak epub option in calibre, delete the css file in the opened epub folder, and recompress it in calibre, followed by a reconversion to epub with your css override.
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