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In my tests, it will reliably pick up the metadata if the PDF version is below 1.5; for documents saved as version 1.5 or newer, it will only work if the metadata object is not part of a compressed object stream. The Kindle can display v1.5 PDFs, but the metadata scanner doesn't know how to find the Info dictionary inside of a compressed object stream.
So either save as version 1.3 or 1.4 (which will produce larger files), or add the metadata after the fact with a tool that does an append-only update rather than rewriting the entire file. pdftk does rewrites, Acrobat does appends unless you "Save as".
Basically, if a simple search of the file reveals an uncompressed object containing the strings /Title and /Author (followed by either plain text in () or hex-encoded Unicode text in <>), the Kindle metadata scanner can see them.
-j
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