How to email DRM-free ebooks to your Amazon Kindle Paperwhite from your PC or Mac

Situation: you have a bunch of DRM-free ebooks on your PC/Mac that you’d like to get to your Kindle Paperwhite, but you don’t have a USB cable handy to transfer them directly. I had some trouble following Amazon’s writeup on how to do this, so I figured I’d write the guide that follows:

1. Add your Gmail address to your Kindle’s Approved Personal Document E-mail List here.
2. On the same page as above, make a note of – after editing, if desired – your Kindle’s email address, found under the Send-to-Kindle Email Settings.
3. Download and install Calibre, preferably the 64-bit build if you’re on Windows x64.
4. If you do NOT wish to email your books directly from Calibre, skip to Step 5. Otherwise: during the installation process, follow the prompts to enter the email address from Step 2 and set up email capability using your Gmail address from Step 1. Other email providers can be used, but Calibre makes it easiest to use Gmail.
5. Follow the rest of the Calibre setup wizard.
6. Launch Calibre:

   

   Calibre is updated weekly, so you’ll want check for updates each time before using it.

7. If the book(s) you want to send aren’t already in the library folder Calibre had you select during Steps 3 to 5, click the Add Books drop down menu and select the appropriate option.
8. Wait for the books to import.
9. When the books have appeared in your Calibre library,  select the titles you want to email.
10. Right-click on your selection. If you’d rather email the files manually, skip to Step 13.
11. Mouse over Connect/share and click Email to [email address from Step 2].
12. Click Yes in the dialog below, and then skip to Step 24:

    

    You’ll want to click Yes here due to the Paperwhite’s horribly limited format support.

13. Mouse over Convert books and then click Convert individually or Bulk convert if you’re converting one book or multiple books, respectively.
14. In the dialog box that follows, click MOBI in the Output Format drop down menu:

    

    Did you know Kindle Paperwhites don’t support the latest MOBI version? Thanks, Amazon.

15. Click MOBI Output.
16. Under Kindle options, select old in the MOBI file type: drop down menu if it wasn’t already selected by default. That’s right, Kindle Paperwhites – even with the newest firmware – choke on the new file type. Go figure.
17. Click OK and wait for the conversion job(s) to complete.
18. For each book you converted, right-click on the title in Calibre’s library list.
19. Click Open containing folder. You’ll find the .mobi output file (1 for each book) there.
20. In Gmail, compose an email to the address in Step 2
21. Enter “convert” (without the quotes) in the email subject line. Don’t forget to do this, or Amazon’s web conversion service will choke on the file(s), even though you’ve already converted them in Calibre.
22. Attach the files from the folders in Step 18.
23. Send the email.
24. Turn your Kindle Paperwhite on:

    

    If you’ve gotten this far without throwing the Kindle against a wall, pat yourself on the back.

25. Touch the Options menu button.
26. Touch Sync and Check for Items.
27. The books should appear under Device.

Personally, I think Paperwhite’s format support and email transfer service is a joke, for several reasons:

• Lack of EPUB support.
• Lack of “new” .mobi support. This is especially ridiculous since the Windows Kindle desktop app supports the format.
• “Old” .mobi files still need conversion in the cloud before being delivered to the end device, which makes no sense at all.
• Lack of AZW3 support. Yeah that’s right: Kindle Paperwhites choke  on 3rd party files in Amazon’s own format.
• Large PDF files will crash the Paperwhite.

The method here may work for other Kindle models, but your mileage may vary.