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The culprit here is DRM. Here's my typical workflow for a non DRM book.
1) Download book
2) Drag and drop into calibre
3) Press convert button
3) Connect reader and wait for conversion to finish (typically 1 minute)
4) Press send to device button
5) Read
Eventually, when I integrate various online books sources into calibre 1) and 2) will be combined into a single step.
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