CODEWITHSUNDEEP
kindlecalibre
G Warner
G Warner

Reputation: 1369

Sending ebooks from Linux Mint to Kindle Paperwhite via Calibre

I'm trying to send some ebooks from my Linux Mint desktio to my kindle paperwhite using Calibre and am getting the error:

Starting job: Email Counter-Clock World to  [email protected] 

Sending failed...

Traceback (most recent call last):
  File "site-packages/calibre/gui2/email.py", line 45, in run
  File "site-packages/calibre/gui2/email.py", line 135, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 137, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 129, in sendmail_direct
IOError: Failed to send mail: error(110, 'Connection timed out')


Retrying in 1 seconds...

Waiting 1 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks 

Sending failed...

Traceback (most recent call last):
  File "site-packages/calibre/gui2/email.py", line 45, in run
  File "site-packages/calibre/gui2/email.py", line 135, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 137, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 129, in sendmail_direct
IOError: Failed to send mail: error(110, 'Connection timed out')

Job: "Email Counter-Clock World to  [email protected]" failed with error: 
Traceback (most recent call last):
  File "site-packages/calibre/gui2/threaded_jobs.py", line 83, in start_work
  File "site-packages/calibre/gui2/email.py", line 102, in __call__
IOError: Failed to send mail: error(110, 'Connection timed out')

Called with args: (u'/tmp/calibre_3.44.0_tmp_RREYM4/VDbQlzcaltmpfmt.mobi', u'Counter-Clock World - Philip K. Dick.mobi', u' [email protected]', u'E-book: Counter-Clock World', u'Attached, you will find the e-book\n\nCounter-Clock World\n\tby Philip K. Dick\n\nin the MOBI format.') {u'abort': , u'notifications': , u'log': }

Sent a test email through calibre with the following settings: "Send email from:" [email protected] (this address is recognized by my amazon account) "Hostname:" smtp.gmail.com "Port:" 25 "username:" [email protected] "Password:" correct password "Encryption:" SSL

and got the error

Traceback (most recent call last):
  File "site-packages/calibre/gui2/wizard/send_email.py", line 209, in test_email_settings
  File "site-packages/calibre/utils/smtp.py", line 149, in sendmail
  File "site-packages/calibre/utils/smtplib.py", line 338, in connect
  File "site-packages/calibre/utils/smtplib.py", line 830, in _get_socket
  File "socket.py", line 575, in create_connection
error: [Errno 101] Network is unreachable


Log:
connect: (u'smtp.gmail.com', 25)
connect: (u'smtp.gmail.com', 25)

Totally at a loss here. Any insight?

Upvotes: 2

Views: 451

Answers (1)

Simón
Simón

Reputation: 455

It seems you're trying to send email with a Gmail account.

As I understand, Google does not allow clients to connect through port 25 (usually reserved for unencrypted SMTP).

On their Gmail Help article about third-party email client settings, they instruct using port 587 with SSL and TLS (I'm not sure if Calibre supports these settings).

Besides that, you'll also need to either:

  • Allow Less Secure Apps access to your Google account (this won't work if you have 2-factor authentication enabled).

  • Create an Application-specific password just for Calibre (this requires having 2-factor authentication enabled).

Upvotes: 0

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