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With a Sony Reader on the Mac there are problems with using anything but the Sony Reader Library.
For Calibre as several people have already mentioned there is no DRM support, and the only other client that currently does DRM support is Adobe Digital Editions.
For ADE, the problem is that it doesn't recognize your Sony Reader, and so won't transfer files directly to it. While this is a minor annoyance for purchased content ( you can do this by copy files in the Finder ), this is a bigger problem for content that you get from a Library. For Library content (on the Mac) you must use Sony Reader Library to transfer your content or you will not be able to view it.
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