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ADE on the Mac specifically does not support the Sony Readers. Assuming you have already authorized your Reader to same AdobeID that you authorized ADE with, you can transfer the ePub or PDF files manually (using the Finder) or using Calibre, however this will not work for content that you get from a Library (that is returnable). For Library content you will need to use the Sony Ebook Library software or use ADE on windows.
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Jim Lester
Adobe Systems
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