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How To Fix Calibre To Kindle Email Delivery Errors?

Calibre works fine but the ‘Send to Kindle’ button fails every time with an email delivery error—anyone have a recent fix? Amazon’s official instructions didn’t solve my EPUB conversion woes.
2025-07-14 15:20:28
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5 Answers

Best Answer
Chelyn Lager
Chelyn Lager
First, check that the Amazon-approved email address for your Amazon account is correct in Calibre. Then check your Amazon account settings under 'Manage Your Content and Devices' for approved senders. Sometimes an error will occur because the file is too large or is in an unsupported file type. MOBI or AZW3 conversions tend to work okay. I’ve recently been reading ‘Alpha’s Regret: Chasing My Rejected Mate’ for a light and quick read that can be easily sideloaded as a file to my Kindle. It’s a very fast-paced story and follows the exiled heroine as she builds a powerful new life. ‘Alpha’s Regret: Chasing My Rejected Mate’ is often available for free to read on a number of different serials sites.
2026-07-31
Delilah
Delilah
I’ve had some problems with email delivery in the past. The first thing to check is whether the email address you are trying to send from has been approved in Amazon’s ‘Approved Personal Document Email List’ within Kindle Personal Document Settings.

This problem can also be caused by the email subject line or the attachment file type. Make sure to use a very simple subject line, for example ‘Convert’, and a Kindle compatible file type, like MOBI or AZW3. As mentioned previously, sometimes ISPs block outgoing emails with attachments. This can be worked around by using an alternative email account, such as a Google Gmail account, instead of your default email account. Also, be sure to check your email account’s spam folder as Amazon’s servers may have redirected the email there. In some cases, simply restarting Calibre and re-creating the book file will also work to solve the problem.
2025-07-18
Bryce
Bryce
This problem was caused by my ISP blocking the port 25 for outgoing emails. In Calibre settings for Kindle, I changed to use port 587 with TLS. Also, I had to change email address for my Kindle from ‘@kindle.com’ to ‘@kindle.’
2025-07-19
Emily
Emily
Most failures to deliver email to Kindle are caused by file size and file type. Emails greater than 50MB to Kindle emailed addresses cannot be delivered due to file size restrictions. Many MOBI files (especially older ones) fail to deliver due to Kindle inability to open MOBI formatted files. The books need to be converted to AZW3 or KFX files prior to sending to Kindle email addresses. Some Delivery Failure messages appear to come from Amazon’s filters when sending from custom domain email addresses (for example: ProtonMail). The issue with failed delivery from custom domain emails can be avoided by sending from more mainstream providers.
2025-07-19
Owen
Owen
I’ve encountered a few errors in sending email from Calibre to Kindle, but there are a few things that can help with these errors. First, the Kindle email address for receiving can change when you modify your Amazon account settings. Be sure to check this before trying to troubleshoot any issues with email sent from Calibre. In ‘Connect/share’ email settings in Calibre for sending email, ensure all of the settings for sending email from your sending email account are entered in exactly. This includes entering the full SMTP server for the account in question, such as ‘smtp.gmail.com’. I’ve wasted hours debugging an issue only to find out that I had entered ‘gmail.com’ instead of ‘smtp.gmail.com’ for the SMTP server. Sending a test email with a small PDF, such as a 1-page pdf, can also help determine if the issue is related to file corruption. Amazon’s Kindle support page for server-side errors has a useful troubleshooting checklist that may also help with these types of errors.
2025-07-20

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