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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  me@free.kindle.com 

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  me@free.kindle.com" 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' me@free.kindle.com', 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:" blah@blah.com (this address is recognized by my amazon account) "Hostname:" smtp.gmail.com "Port:" 25 "username:" myemail@gmail.com "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?

G Warner
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1 Answers1

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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).

Simón
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