Calibre One-Click Email Delivery to Kindle: Complete Setup Guide & Troubleshooting
Kindle Mate previously published a tutorial titled “Delivering Documents to Kindle via Email Attachments”, which covers manually sending e-books to Kindle via email. This guide introduces an even more convenient method—using Calibre’s built-in email delivery feature for one-click sending.
Table of Contents
Follow the steps below to set up and enjoy the convenience of one-click delivery.
Deep Dive
Books & Literature
Kindle Oasis
Beginner’s Guide
Part 1: Delivery Setup & Step-by-Step Instructions
Before you begin, ensure you have a working email address and that your Kindle device is registered to your Amazon account. If you don’t have an Amazon account, click here (Amazon China) or click here (Amazon US) to register first. For detailed instructions, refer to Delivering Documents to Kindle via Email Attachments.
1. Download and Install Calibre
Calibre supports multiple operating systems. Download the version that matches your system:
Deep Dive
ebook
Download Calibre: https://bookfere.com/tools#calibre
2. Add the Recipient Email Address
Click the Preferences icon, locate the Share category, and click Sharing books by email. In the dialog that appears, click the Add email button on the right, then enter the Kindle delivery address associated with your device (multiple addresses can be added). The recipient email address can be found in Manage Your Content and Devices under the Devices tab.
Note that Kindle now supports EPUB delivery. To prevent Calibre from automatically converting EPUB to MOBI, remove MOBI from the Format field when adding the email address, leaving only EPUB.
▲ Change the format to EPUB to avoid automatic MOBI conversion
3. Enter the Sender Email Address
In the Sender address field, enter your email address. Ensure this email has been added to Amazon’s Approved Personal Document E-mail List on the Settings page in your Kindle Management console (this option is at the bottom of the Settings page).
4. Configure the Email Server
For Gmail users, simply click the Gmail icon, enter your email address and password, and Calibre will auto-fill the hostname and port. For other providers, manually enter the server settings along with your email username and password. Common email server configurations:
Provider Hostname Port Encryption Notes Gmail smtp.gmail.com 465 / 587 SSL / TLS * VPN required in China
* Must enable 2FA and use app-specific password 163.com smtp.163.com 465 / 587 SSL * New accounts may be restricted
* Use authorization code (not login password)
* Frequent sending may trigger SMTP ban 126.com smtp.126.com 465 / 587 SSL — Yeah.net smtp.yeah.net 465 / 587 SSL — QQ.com smtp.qq.com 465 SSL * Use authorization code (not login password)
Tip 1: Ensure the port number is entered correctly—465 or 587, not 456 or 578.
Tip 2: Attachment size limits: Gmail 25MB; most others 50MB.
Email parameter configuration example:
5. Test Email Sending
After configuration, click the Test email sending button at the bottom-right. A security prompt will appear—confirm to proceed. In the test dialog, click Test. If the display shows “Email sent,” your setup is successful. Click OK to close the dialog, then click Apply in the upper-left corner to save your settings.
* Shortly after the test email is sent, Amazon’s automated system will send a message titled “You sent an email to Kindle without any file attachments”—this is normal and can be ignored.
6. One-Click Book Delivery
Return to the main library view, select one or more e-books, right-click the selection, hover over Connect/share in the context menu, then click Send to ***@kindle.cn (the address added in Step 2). Calibre will handle the rest, and your books will appear in your Amazon Content library.
Once you’ve converted EPUB or other formats to MOBI, a single right-click delivers them to the cloud—it’s that simple. Give it a try!
Part 2: Troubleshooting & Common Errors
If delivery fails, double-check that both the Sender address and the Username in server settings are complete email addresses (e.g., example@domain.com). Neither field should be just the prefix or the domain alone.
Also verify that the port number is correct: for SSL encryption, use port 465 or 587; for Gmail TLS, use port 587.
If you encounter any of the following errors during testing or delivery, refer to the corresponding solutions below:
Error 1
SMTPAuthenticationError: (550, ‘\xd3\xc3\xbb\xa7\xb1\xbb\xcb\xf8\xb6\xa8′)Solution:
The garbled text means “User locked.” This often occurs with new 163.com accounts, as SMTP client access is disabled by default. To enable it: log in to 163.com webmail → Settings → POP3/SMTP/IMAP → enable SMTP mail service (mobile verification may be required).
Error 2
SMTPAuthenticationError: (454, ‘Authentication failed, please open smtp flag first!’)
SMTPAuthenticationError: (535, ‘Error: authentication failed’)Solution:
For QQ Mail: log in to the web version → Settings → POP3/IMAP/SMTP/Exchange/CardDAV/CalDAV Services → enable POP3/SMTP Service.
For 163.com: follow the same steps as Error 1 above.
Error 3
SMTPServerDisconnected: Connection unexpectedly closedSolution:
This is a known issue with QQ Mail’s SMTP. Switch to another provider such as 163.com.
Error 4
reply: ‘535 Error: authentication failed\r\n’
reply: retcode (535); Msg: Error: authentication failedSolution:
Check if Client Authorization Password is enabled for your email account. If so, you must use the authorization code instead of your login password.
Error 5
554 DT:SPMSolution:
This error is common with 163.com. The official explanation: the email content contains disallowed information or has been flagged as spam. This may result from bulk sending. If encountered, switch to another email provider.
Error 6
500 Error: bad syntax\r\n5.5.4 Invalid domain nameSolution:
This may occur on Windows due to a space in the “Connection-specific DNS suffix” network property. Go to Control Panel → Network and Sharing Center → click your active connection → Details → check if the DNS suffix contains a space. If so, click Properties → double-click Internet Protocol Version 4 (TCP/IPv4) → Advanced → DNS tab → clear or change the DNS suffix to HOST, then confirm and save. via
For more detailed steps, refer to Fixing Calibre “500 Error: bad syntax”.
Error 7
error: [Errno 10060]Solution:
Connection failed. Check if your computer is using a proxy, or if a firewall or antivirus is blocking SMTP connections.
Error 8
SMTPSenderRefused: (553, ‘Mail from must equal authorized user’, u’1584624613@qq.com’)Solution:
The SMTP server rejected the request because the sender email and sender name do not match. If your email is example@163.com, the sender name must also be example@163.com—not just “example” or another address. Use your full email address as the username.
Error 9
File “ssl.py”, line 828, in do_handshake
error: [Errno 10054]Or
File “socket.py”, line 575, in create_connection
error: [Errno 10060]Solution:
Connection failed. Causes vary by environment. Check proxy settings, firewall, and antivirus software for SMTP interference.
Error 10
smtplib.SMTPDataError: (554, b’DT:SPM 163 smtp12,EMCowABXfZ1YQGphxxyIEQ–.191S2 1634353251,please see http://mail.163.com/help/help_spam_16.htm?ip=127.0.0.1&hostid=smtp12&time=1634353251′)Solution:
This error is common with 163.com. The error code 554 and the bounce code explanation indicate:
554 DT:SPM — The email content contains disallowed information or has been flagged as spam. Check whether any virus or spam has been sent.
Certain behaviors may trigger 163.com’s spam restrictions. The quickest fix is switching to a more permissive provider like Gmail.
Error 11
OSError: Failed to send mail: SMTPRecipientsRefused({‘xxx@kindle.com’: (550, b’5.7.1 IP address blacklisted by recipient’)})Solution:
The sending IP address has been blacklisted by the recipient. Verify you’re using the official SMTP service from your email provider. If you are and still encounter this error, try switching to a different provider.
Part 3: Fixing Pinyin Book Titles
Books delivered via Amazon’s five Send to Kindle methods display the filename at the time of delivery. Calibre automatically converts Chinese filenames to Pinyin with no built-in option to disable this behavior, resulting in Pinyin titles appearing on your Kindle.
Bookfere has developed a Calibre plugin called Send to Kindle to fix this issue. For details, refer to How to Fix Pinyin Book Titles When Delivering Chinese Books via Calibre.
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