This may be a silly question, but are these two ADE software the same version ? The Mac version of ADE has been updated recently, IIRC...
Anyway, this should work ; you don't have to use either ADE or Calibre to upload the file to your PRS, a simple copy should be enough ; but you must register the PRS with the same copy of ADE that you'll take this file from (I wonder if I'm clear?).
To say it differently : download your book, put it in ADE (wherever), make sure you registered your reader with THIS copy of ADE (whichever it is) and either 1/ drag and drop the ebook into your reader in ADE or 2/ find the ePub file, and copy this file to yor device.
Hope this helps !
Cheers,
David.
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