I've just received a kindle. I bought a book on Google Play Book.

I downloaded the book from play book in .ascn, converted to PDF with the adobe program, removed the DRM.

Now I have a working PDF (I can see correctly on my macbook), but is bigger than 50MB, and I can't upload with send to kindle program. I compressed it and obtained a 28MB that I tried to upload to the kindle, but I didn't receive the book. I also tried with send to kindle through mail @kindle.com but I received an error response mail.

Gentile Cliente,

Non è stato possibile consegnare il seguente documento inviato in data 05:57 PM alle ore gio, ott 13, 2016 GMT, al Kindle specificato: * ldm.pdf

Con il Servizio Documenti Personali Kindle puoi convertire e inviare i seguenti formati di file: Microsoft Word (.doc, .docx) Rich Text Format (.rtf) HTML (.htm, .html) Documenti di testo (.txt) Documenti archiviati (zip , x-zip) e documenti archiviati compressi Mobi

What can be the issue?

3 Answers 3


First, what type of Kindle do you have? Do you have e-ink device or a Kindle tablet (i.e, Kindle Fire)?

If you have a Kindle tablet, then I recommend that you view the file with a PDF reader app instead of using the Kindle app. If there is a cloud-based app, that is even better.

File size is another problem -- PDF readers can typically read larger PDF files, but it is still difficult to transfer to the device. Perhaps you can use dropbox or gmail to send it, but I'm guessing you can open it through the browser in your tablet.

You have highlighted a very important problem on Kindles. I believe Google Play Books (GPB) is the best reading system across platforms, and it's crazy that there is no GPB app on Kindle (ios has a GPB app which works great).

Some places on the Net suggest a way to install Google Play store on Kindle by sideloading, and that is good, but I don't think that is an effective way to get GPB on your kindle. (I recommend against it -- though I wish Google and Amazon.com can figure out a solution....)

  • I have an e-ink kindle
    – Mitro
    Commented Oct 14, 2016 at 6:46
  • I would focus more on reducing file size of PDF -- because even if you could transfer a 50+mb PDF, many e-ink devices will not render such large files easily. I would look for online services which can reduce file size. A quick google check shows www.smallpdf.com, www.compress.pdf , etc. I have never tried any of them. I'm sure Adobe Acrobat has this feature as well. If possible I would try to reduce it to less than 10MB, but the final results may not be good. Commented Oct 14, 2016 at 16:56

Converting an EPUB book to a PDF file is usually a bad idea, unless you want to print the book.

Install Calibre, add the EPUB, remove the DRM, convert it to an AZW3 book and have Calibre send the book to your Kindle via USB cable.

If you still want to use the PDF file, you'll have to copy it to the Kindle documents folder via a USB cable because Kindle Personal Documents Service doesn't support PDF files.

However, the built-in Kindle PDF app is extremely limited.


As far as I can tell (my Italian is mostly restricted to things you need to know to understand training instructions), you cannot send PDF files, but only the indicated formats (.doc, .docx, .rtf, .htm, .html, .txt, .zip , .x-zip, .mobi).

Try removing the images from the file before direct uploading PDF, convert to a supported format (.mobi e.g. with Calibre) and/or use OCR on the text.

OCR might be necessary as an A4 text page uses about 2Kb of uncompressed bytes and a 50Mb file could so be more than 250000 pages. PDF is inefficient but not that inefficient. Convert to .mobi in Calibre and if the output file still is multiple megabytes, you probably are dealing with images instead of text (or you have may photos etc in the text), in that case use OCR.

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