Alas, two challenges exist. First, services such as Gmail may yank away your account if you overwhelm their servers with emailed books. Luckily Calibre comes with throttling. But that’s still a pain. No easy solution here.
The second hassle is that Gmail and brethren in recent years have made it harder for apps to perform such tasks. The claimed reason is security. Calibre boosters say the real reason could be a desire to drive people to the services’ own tools. Whatever the case, fear not! A fix does exist. You can just sign up for a more Calibre-friendly service called GMX. Here’s a quick summary of the steps:
1. From Calibre’s main menu, go to Preferences, then Sharing books by email.
2. Provide the email address of your Kindle (take care of business in Steps 8 and beyond if you don’t have one). Formats will be AZW, MOBI, TPZ, PRC, AZWI. Auto send should be checked.
3. You can then choose Use GMX, which will enter much of the information automatically.
4. Fill in Send email from with your e-mail address.
5. Then, for the Hostname, enter mail.gmx.com, and for the port enter 587, if the right information isn’t there already.
6. Fill in your GMX e-mail address as the user name.
7. Provide your GMX password.
8. Specify TLS as the encryption method.
7. Click on the Apply in the lower right hand corner.
8. If you lack a Kindle address, go to the Amazon site and within Your account click on Manage your content and Devices and then on Your Devices. Choose your device and enter an e-mail address. Of course, chances are that your Kindle came with an address. But now you’ll know how to edit it.
9. Even if you already have a Kindle address, you’ll still need to give permission for it to receive messages from GMX in particular. Within Manage Y our Content and Devices, click on Settings.
10. Within Settings, you’ll see a bunch of options, including Personal Document Settings, where you can edit e-mail addresses for various devices, just as you can through the means described in Step #8. But keep scrolling down until you see Approved Personal Document E-mail List. After the existing addresses possibly already listed there, you’ll find Add a new approved e-mail address. Add your new GMX address, and you’re done.
11. Go back to Calibre’s Sharing books by email area and use the test option to see if you’ve succeeded.
Everything clear? Or find an error in the above? Post a comment, and we’ll tweak these directions to perfection.