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I have this ebook that I'm trying to send to my Kindle from my Mac. I've done this before; Get a pdf, send it to Kindle address, and make sure the subject is "convert". This causes Amazon to convert the .pdf to a .azw. Great, easy.

Now I have a pdf that's too big to attach (barely, limit is 25.0MB, and it's 36.2MB). I looked around for ways to compress it:

WTH

So I have a question that could be answered in multiple ways because all I'm trying to do is get this pdf onto my kindle in a reasonable format.

Why is this happening?

What else can I do if this won't work?

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    The data in many image file formats is already compressed, so there's not much that can be done except to reduce the image quality to make them smaller. An alternative might be, if it's a multipage document, to split it into individual pages.
    – martineau
    Commented Jan 28, 2014 at 20:39
  • It is a multipage document. How would I do that?
    – michaelsnowden
    Commented Jan 28, 2014 at 20:40
  • I have Acrobat Professional, which can do that. I'm sure there are free utilities available that can do the same -- just don't know what they might be, sorry.
    – martineau
    Commented Jan 28, 2014 at 20:42
  • Here's a free online PDF splitter.
    – martineau
    Commented Jan 28, 2014 at 20:46
  • Here's some free software called PDFsam (PDF Split and Merge) someone in a thread on an Adobe forum recommends. There's Windows and MacOS versions of it for download from here
    – martineau
    Commented Jan 28, 2014 at 20:55

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As an above commenter mentioned, professionally published eBook PDFs, and the images they contain, are usually about as optimized as they can be. I don't know what ColorSync is, or does, but it seems like you're using it to solve the wrong problem in this particular case. Rather than fussing with the images at all, split the document up.

Adobe Acrobat retails for a little over $100 USD, and is overkill. I know on previous versions of OSX you could "Print to PDF" (kb article), but I'm afraid don't know if you can select what pages to print with this option, as I haven't had access to OSX in several years.

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  • You can still "Print to PDF" is OS X 10.9.1 (Mavericks), however -- and not surprisingly -- you can't do that from the free Acrobat/Adobe Reader, and there doesn't seem to be any way to extract or save a subset of the file you are viewing. Some other view might be able to do this, but again, the quality of it's output is an unknown.
    – martineau
    Commented Jan 29, 2014 at 2:22

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