Calibre email fails

[EightWeight]

I have tried to get email to work in Calibre so I can send books to my Kindle using different servers and it always fails. Here is the error output:

calibre, version 2.12.0 (linux2, isfrozen: True)
Failed to email book: Failed: Email Patriot Games to *****@free.kindle.com

Starting job: Email Patriot Games to *****@free.kindle.com 

Sending failed...
 
Traceback (most recent call last):
  File "site-packages/calibre/gui2/email.py", line 43, in run
  File "site-packages/calibre/gui2/email.py", line 124, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 116, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 108, 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 43, in run
  File "site-packages/calibre/gui2/email.py", line 124, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 116, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 108, in sendmail_direct
IOError: Failed to send mail: error(110, 'Connection timed out')
 
Job: "Email Patriot Games to *****@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 98, in __call__
IOError: Failed to send mail: error(110, 'Connection timed out')
 
Called with args: (u'/tmp/calibre_2.12.0_tmp_tZX_ks/vONIbfcaltmpfmt.mobi', u'Patriot Games - Clancy, Tom.mobi', u'*****@free.kindle.com', u'E-book: Patriot Games', u'Attached, you will find the e-book\n\nPatriot Games\n\tby Clancy, Tom\n\nin the MOBI format.') {u'abort': <threading._Event object at 0xa90428cc>, u'log': <calibre.utils.logging.GUILog object at 0xa9196b0c>, u'notifications': <Queue.Queue instance at 0xa904254c>}

I have checked and re-checked the server settings, passwords, etc. and all is correct. I looked for the files referenced in the log (email.py, etc.) and they are .pyo files. That's no help to me.

Also there is a reference to "via Preferences->Tweaks". Where in Calibre is that???? Ctrl-p brings up a lot of stuff, but nothing is labeled Tweaks. Is that just a Windows thing?

[DoctorOhh]

Originally Posted by EightWeight

Also there is a reference to "via Preferences->Tweaks". Where in Calibre is that???? Ctrl-p brings up a lot of stuff, but nothing is labeled Tweaks. Is that just a Windows thing?

If when looking at preferences you scroll down you will see tweaks.

[eschwartz]

Go to the email configurator and use the Test email option, which will give more clues as to what is going wrong.

Post the output with email username and password redacted.

[theducks]

Did I see:
1 second

IIRC the default is 5 Minutes for the stated reason

[EightWeight]

OK, I found Tweaks, duh. Feel like a doofus.

As to the email thing - the test function crashes on me. I tried SSL encryption and that solved the problem for me!