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Old 10-13-2012, 12:52 PM   #1
TarraAnn85
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Exclamation [Old Thread] Calibre Will Not Send Books To Kindle

For the past say month i have been unable to send books from calibre to my kindle. Thinking maybe it was just me i had my friend who also uses Calibre try and send one to hers and she had she same problem. It will act like its sending but 5 minutes later will still be doing so and then i end up with a error. Here is the latest error i have gotten:

Starting job: Email Beautiful Disaster to xyzzy@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '220 mx.google.com ESMTP la6sm9283216qeb.8\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP la6sm9283216qeb.8
connect: mx.google.com ESMTP la6sm9283216qeb.8
send: 'ehlo [192.168.1.2]\r\n'
reply: '250-mx.google.com at your service, [24.148.198.56]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [24.148.198.56]
SIZE 35882577
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 37, in run
File "site-packages\calibre\gui2\email.py", line 114, in sendmail
File "site-packages\calibre\utils\smtp.py", line 107, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 637, in starttls
File "ssl.py", line 381, in wrap_socket
File "ssl.py", line 143, in __init__
File "ssl.py", line 305, in do_handshake
SSLError: [Errno 8] _ssl.c:504: EOF occurred in violation of protocol


Retrying in 301 seconds...

connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '220 mx.google.com ESMTP dr8sm10093202qab.11\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP dr8sm10093202qab.11
connect: mx.google.com ESMTP dr8sm10093202qab.11
send: 'ehlo [192.168.1.2]\r\n'
reply: '250-mx.google.com at your service, [24.148.198.56]\r\n'
reply: '250-SIZE 35882577\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [24.148.198.56]
SIZE 35882577
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
Sending timed out
Job: "Email Beautiful Disaster to xyzzy@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 84, in __call__
Exception: Sending email u'E-book: Beautiful Disaster' to u'xyzzy@kindle.com' timed out, aborting

Called with args: (u'C:\\Users\\Tarra\\AppData\\Local\\Temp\\calibre _0.9.2_tmp_ydm8n0\\6rdfzkcaltmpfmt.mobi', u'Beautiful Disaster - Jamie McGuire.mobi', u'xyzzy@kindle.com', u'E-book: Beautiful Disaster', u'Attached, you will find the e-book\n\nBeautiful Disaster\n\tby Jamie McGuire\n\nin the MOBI format.') {u'notifications': , u'abort': , u'log': }



My friend gets the same error when she tries from her Calibre. If anyone can help it would be greatly appreciated. Thanks in advance!

Last edited by theducks; 10-13-2012 at 02:11 PM.
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Old 10-13-2012, 05:46 PM   #2
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Calibre doesn't handle the twostep auth you enabled for your Google account.

Use another mail provider as the sender, or send your book via another way (USB?).
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Old 10-18-2012, 09:55 PM   #3
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or disable the 20-step auth?

gmail works fine for me.
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Old 10-19-2012, 03:45 AM   #4
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You can leave the 2 step auth in, however go and get a unique password for calibre. There is a full explanation on the page you went to, to enable 2 step auth. It's a great thing to leave on, just get an application specific password for calibre. I have, and it works fine.
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Old 10-19-2012, 01:57 PM   #5
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@ianw: Thanks for the confirmation, I didn't bother to check if it that would have been enough .
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Old 10-20-2012, 06:49 PM   #6
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Exclamation

Hi,
Well i dont usually use gmail for sending them out i use AOL. But it was doing the same thing so i tried my yahoo account, didn't work, tried my Windows Live account, didn't work, so i was left with Gmail. Where would i go exactly to get the calibre unique password? I don't know where to go to do that. I just retried after setting it back to my AOL account and got this FAILED error:

Starting job: Email Beautiful Disaster to TarraAnn85@kindle.com
connect: (u'smtp.aoll.com', 587)
connect: (587, u'smtp.aoll.com')

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 37, in run
File "site-packages\calibre\gui2\email.py", line 114, in sendmail
File "site-packages\calibre\utils\smtp.py", line 105, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 281, in _get_socket
File "socket.py", line 571, in create_connection
error: [Errno 10061] No connection could be made because the target machine actively refused it


Retrying in 1 seconds...

connect: (u'smtp.aoll.com', 587)
connect: (587, u'smtp.aoll.com')

Sending failed...

Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 37, in run
File "site-packages\calibre\gui2\email.py", line 114, in sendmail
File "site-packages\calibre\utils\smtp.py", line 105, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 281, in _get_socket
File "socket.py", line 571, in create_connection
error: [Errno 10061] No connection could be made because the target machine actively refused it

Job: "Email Beautiful Disaster to TarraAnn85@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 92, in __call__
error: [Errno 10061] No connection could be made because the target machine actively refused it

Called with args: (u'C:\\Users\\Tarra\\AppData\\Local\\Temp\\calibre _0.9.3_tmp_q7ui4e\\ie7ryscaltmpfmt.mobi', u'Beautiful Disaster - Jamie McGuire.mobi', u'TarraAnn85@kindle.com', u'E-book: Beautiful Disaster', u'Attached, you will find the e-book\n\nBeautiful Disaster\n\tby Jamie McGuire\n\nin the MOBI format.') {u'notifications': <Queue.Queue instance at 0x08024558>, u'abort': <threading._Event object at 0x07FD2B70>, u'log': <calibre.utils.logging.GUILog object at 0x07FD2AD0>}

And if none of those email options work with Calibre what kind of email account will if i cannot find where to get the unique password. I have used basically all the popular ones.
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Old 10-20-2012, 06:57 PM   #7
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@TarraAnn85: That's another error entirely, happening later, from Amazon's side, AFAICT.

Make sure the kindle email is actually correct & properly set on your 'Manage Your Kindle' page, and that the email address you're using in Calibre is whitelisted on the 'Manage Your Kindle' email settings.
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Old 10-20-2012, 07:10 PM   #8
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Hi just checked the setting in calibre and when i had switched it back over to AOL i had made some typing errors, but i fixed it and tried sending again and got this after 5 minutes of nothing:

Starting job: Email Beautiful Disaster to TarraAnn85@kindle.com
connect: (u'smtp.aol.com', 587)
connect: (587, u'smtp.aol.com')
reply: '220-mtaout-ma03.r1000.mx.aol.com ESMTP MUA/Third Party Client Interface\r\n'
reply: '220-AOL and its affiliated companies do not\r\n'
reply: '220-authorize the use of its proprietary computers and computer\r\n'
reply: '220-networks to accept, transmit, or distribute unsolicited bulk\r\n'
reply: '220-e-mail sent from the internet.\r\n'
reply: '220-Effective immediately:\r\n'
reply: '220-AOL may no longer accept connections from IP addresses\r\n'
reply: '220 which no reverse-DNS (PTR record) assigned.\r\n'
reply: retcode (220); Msg: mtaout-ma03.r1000.mx.aol.com ESMTP MUA/Third Party Client Interface
AOL and its affiliated companies do not
authorize the use of its proprietary computers and computer
networks to accept, transmit, or distribute unsolicited bulk
e-mail sent from the internet.
Effective immediately:
AOL may no longer accept connections from IP addresses
which no reverse-DNS (PTR record) assigned.
connect: mtaout-ma03.r1000.mx.aol.com ESMTP MUA/Third Party Client Interface
AOL and its affiliated companies do not
authorize the use of its proprietary computers and computer
networks to accept, transmit, or distribute unsolicited bulk
e-mail sent from the internet.
Effective immediately:
AOL may no longer accept connections from IP addresses
which no reverse-DNS (PTR record) assigned.
send: 'ehlo [192.168.1.2]\r\n'
reply: '250-mtaout-ma03.r1000.mx.aol.com\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-SIZE 36700160\r\n'
reply: '250-ETRN\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-AUTH LOGIN XAOL-UAS-MB PLAIN\r\n'
reply: '250-AUTH=LOGIN XAOL-UAS-MB PLAIN\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-8BITMIME\r\n'
reply: '250 DSN\r\n'
reply: retcode (250); Msg: mtaout-ma03.r1000.mx.aol.com
PIPELINING
SIZE 36700160
ETRN
STARTTLS
AUTH LOGIN XAOL-UAS-MB PLAIN
AUTH=LOGIN XAOL-UAS-MB PLAIN
ENHANCEDSTATUSCODES
8BITMIME
DSN
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
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Old 10-21-2012, 12:03 PM   #9
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Use gmail. AOL has always been proprietary and apparently doesn't let you use a 3rd party emailer (I'm always surprised that they even let you access the entire internet now, for that matter).

Set up a special account, just for this and don't turn on the 2-part auth (and note that using that probably blocks real people from sending you mail, since the 'authorize' msg gets deleted by the sender by habit -- I assume any such I get are actually either phishing attempts or link to a virus laden site and never use them anymore).

Then, make sure you have added that new, special email to the Kindle authorized email list on your account. the first msg you had sounded like you are skipping this step.

Then, test it by using gmail itself to email a book to your kindle email address. Once that works, then set up calibre to use your new address. You can then ignore that account forever, other than to go over now and then and move all sent messages to the trash (to keep your space used down).
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Old 10-22-2012, 05:57 PM   #10
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Thanks i made a new email addy on gmail just for my kindle. Test email worked. But before i go to set it up on Calibre how do i make sure that the 2-part auth is not turned on? I do not know how to make sure its not on.

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Old 10-23-2012, 04:02 AM   #11
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I don't think it is on by default (I've never used it) - just let Calibre do the setup for gmail and run the Test function to make sure it is working.
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Old 11-02-2012, 09:29 AM   #12
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I don't think it's too complicated to get around this. Following advice I found elsewhere, I simply generated an application-specific password for Calibre through my Gmail account (which is set to 2-step verification), then copied that password, went to Calibre -> preferences -> sharing -> sharing books by email, and put it into the password box instead of my usual Gmail password. hey presto, and I could send ebooks to my Kindle via Calibre again.
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Old 11-10-2012, 11:16 AM   #13
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And how do i generate a application-specific password for Calibre?
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Old 11-10-2012, 12:16 PM   #14
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Ok i found how to do the Application specfic password and it didn't fix the issue. So i turned the 2-step verification back off. Another thing is when i try and do a test email through calibre the whole program freezes up and i end up having to restart the program. Also using the new email address that i made specifically for Calibre does not work either. It still does not send.
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Old 11-10-2012, 12:32 PM   #15
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Just an update, after 15 minutes of waiting for the book to send through Calibre, using the new email address i got this message:

Starting job: Email Beautiful Disaster to TarraAnn85@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
Sending timed out
Job: "Email Beautiful Disaster to TarraAnn85@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 84, in __call__
Exception: Sending email u'E-book: Beautiful Disaster' to u'TarraAnn85@kindle.com' timed out, aborting

Called with args: (u'C:\\Users\\Tarra\\AppData\\Local\\Temp\\calibre _0.9.6_tmp_x91uh3\\3g7nkbcaltmpfmt.mobi', u'Beautiful Disaster - Jamie McGuire.mobi', u'TarraAnn85@kindle.com', u'E-book: Beautiful Disaster', u'Attached, you will find the e-book\n\nBeautiful Disaster\n\tby Jamie McGuire\n\nin the MOBI format.') {u'notifications': , u'abort': , u'log': }
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