I can't email books to my Kindle device

[corke1]

calibre, version 3.20.0 (darwin, embedded-python: True)

Failed to email book: Failed: Email Bill O'Reilly's Legends and Lies to ads_20b1c3@kindle.com

Starting job: Email Bill O'Reilly's Legends and Lies to ads_20b1c3@kindle.com 

Sending failed...
 
Traceback (most recent call last):
  File "site-packages/calibre/gui2/email.py", line 44, in run
  File "site-packages/calibre/gui2/email.py", line 134, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 135, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 127, in sendmail_direct
IOError: Failed to send mail: error(60, 'Operation 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 44, in run
  File "site-packages/calibre/gui2/email.py", line 134, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 135, in sendmail
  File "site-packages/calibre/utils/smtp.py", line 127, in sendmail_direct
IOError: Failed to send mail: error(60, 'Operation timed out')
 
Job: "Email Bill O'Reilly's Legends and Lies to ads_20b1c3@kindle.com" failed with error: 
Traceback (most recent call last):
  File "site-packages/calibre/gui2/threaded_jobs.py", line 84, in start_work
  File "site-packages/calibre/gui2/email.py", line 101, in __call__
IOError: Failed to send mail: error(60, 'Operation timed out')
 
Called with args: (u'/var/folders/xz/6pxb1k294739wz6_s0bwvzgw0000gn/C/calibre_3.20.0_tmp_S8D9ZT/xbEq_Wcaltmpfmt.MOBI', u"Bill O'Reilly's Legends and Lies - David Fisher.MOBI", u'ads_20b1c3@kindle.com', u"E-book: Bill O'Reilly's Legends and Lies", u"Attached, you will find the e-book\n\nBill O'Reilly's Legends and Lies\n\tby David Fisher\n\nin the MOBI format.") {u'abort': <threading._Event object at 0x119e07290>, u'log': <calibre.utils.logging.GUILog object at 0x11b2f7150>, u'notifications': <Queue.Queue instance at 0x119e15cb0>}

[Barbara1955]

IF they are in Calibre plug your Kindle into the PC & Side load them.

[corke1]

The Kindle apps are on my iPhone and iPad. I cannot plug them into my PC (I use a Mac) because they are not Kindle devices.

[kovidgoyal]

https://manual.calibre-ebook.com/faq...-using-calibre

[sheona18]

Hi,

I've been having the same issue. I used to be able to send the ebooks to my kindle using my email address, but yesterday I tried to do it and it failed to send. An error message would pop up (same as OP). I have followed the instructions found in the link from the above post and made a gmx account and added this account to send from my kindle. After a few mins of trying to send the ebook to my kindle, calibre displays the following message:

Job: "Email Aristotle and Dante Discover the Secrets of the Universe to SHEONA.SOANS_6632F2@KINDLE.COM" failed with error:
Traceback (most recent call last):
File "site-packages/calibre/gui2/threaded_jobs.py", line 84, in start_work
File "site-packages/calibre/gui2/email.py", line 101, in __call__
SMTPAuthenticationError: (535, 'Authentication credentials invalid')

I have transferred the ebooks to my kindle by connecting it to my mac, but these ebooks will not show up on the kindle app on my phone when I try to sync it. I've never had these issues with Calibre/ Kindle before. Any help or advice would be much appreciated

[kovidgoyal]

You've entered an incorrect username/password for your gmx acount. Remember the username is the full gmx email address.

[sheona18]

Thank you, it seems to be working fine now