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Old 12-29-2010, 07:42 PM   #1
bdrawve
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Device: kindle
Email Problems

Okay so I got a Kindle for xmas and also got access to over 600 ibooks from a friend who has downloaded them. Of course I want to at least get some over to my kindle for free so I downloaded Calibre. I went through the whole process and set it all up as well a gmail account. I converted one book for a test run and keep getting the following errrors.? Please bare with me as I am not the most computer savy person....

mail Blink: The Power of Thinking Without Thinking to brdrawve@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '220 mx.google.com ESMTP i2sm13064335icv.3\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP i2sm13064335icv.3
connect: mx.google.com ESMTP i2sm13064335icv.3
send: 'ehlo BrettyD-PC.hsd1.ca.comcast.net.\r\n'
reply: '250-mx.google.com at your service, [67.164.48.69]\r\n'
reply: '250-SIZE 35651584\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, [67.164.48.69]
SIZE 35651584
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
send: 'ehlo BrettyD-PC.hsd1.ca.comcast.net.\r\n'
reply: '250-mx.google.com at your service, [67.164.48.69]\r\n'
reply: '250-SIZE 35651584\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [67.164.48.69]
SIZE 35651584
8BITMIME
AUTH LOGIN PLAIN XOAUTH
ENHANCEDSTATUSCODES
send: AUTH <censored>
reply: '535-5.7.1 Username and Password not accepted. Learn more at \r\n'
reply: '535 5.7.1 http://mail.google.com/support/bin/a...y?answer=14257 i2sm13064335icv.3\r\n'
reply: retcode (535); Msg: 5.7.1 Username and Password not accepted. Learn more at
5.7.1 http://mail.google.com/support/bin/a...y?answer=14257 i2sm13064335icv.3

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 110, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 608, in login
SMTPAuthenticationError: (535, '5.7.1 Username and Password not accepted. Learn more at\n5.7.1 http://mail.google.com/support/bin/a...y?answer=14257 i2sm13064335icv.3')

Retrying in 301 seconds...
connect: (u'smtp.gmail.com', 587)
connect: (587, u'smtp.gmail.com')
reply: '220 mx.google.com ESMTP q13sm21600556wfc.5\r\n'
reply: retcode (220); Msg: mx.google.com ESMTP q13sm21600556wfc.5
connect: mx.google.com ESMTP q13sm21600556wfc.5
send: 'ehlo BrettyD-PC.hsd1.ca.comcast.net.\r\n'
reply: '250-mx.google.com at your service, [67.164.48.69]\r\n'
reply: '250-SIZE 35651584\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, [67.164.48.69]
SIZE 35651584
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
send: 'ehlo BrettyD-PC.hsd1.ca.comcast.net.\r\n'
reply: '250-mx.google.com at your service, [67.164.48.69]\r\n'
reply: '250-SIZE 35651584\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN XOAUTH\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [67.164.48.69]
SIZE 35651584
8BITMIME
AUTH LOGIN PLAIN XOAUTH
ENHANCEDSTATUSCODES
send: AUTH <censored>
reply: '535-5.7.1 Username and Password not accepted. Learn more at \r\n'
reply: '535 5.7.1 http://mail.google.com/support/bin/a...y?answer=14257 q13sm21600556wfc.5\r\n'
reply: retcode (535); Msg: 5.7.1 Username and Password not accepted. Learn more at
5.7.1 http://mail.google.com/support/bin/a...y?answer=14257 q13sm21600556wfc.5

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 110, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 608, in login
SMTPAuthenticationError: (535, '5.7.1 Username and Password not accepted. Learn more at\n5.7.1 http://mail.google.com/support/bin/a...y?answer=14257 q13sm21600556wfc.5')

Could it be my firewall or email not allowing it to connect....I see that it mentions wrong user name and passwords as well??? From the address to be sent from all that entered was my new username@gmail.com .....left all the defaults the same and entered my email password below other prompts.

I have it going to my @kindle.com account from my newly created gmail account. Did I set something wrong up in the gmail configuration?

Please help.

Thanks!
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Old 12-29-2010, 07:53 PM   #2
bdrawve
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Posts: 8
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Device: kindle
Tweaked it a little again and got this error message this time....

mail Blink: The Power of Thinking Without Thinking to brdrawve@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (u'smtp.gmail.com', 587)

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 103, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 776, in _get_socket
File "ssl.py", line 342, in wrap_socket
File "ssl.py", line 121, in __init__
File "ssl.py", line 281, in do_handshake
SSLError: [Errno 1] _ssl.c:499: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol

Retrying in 301 seconds...
connect: (u'smtp.gmail.com', 587)
connect: (u'smtp.gmail.com', 587)

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 103, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 776, in _get_socket
File "ssl.py", line 342, in wrap_socket
File "ssl.py", line 121, in __init__
File "ssl.py", line 281, in do_handshake
SSLError: [Errno 1] _ssl.c:499: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
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Old 12-29-2010, 08:15 PM   #3
Dopedangel
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Go to your gmail account settings and check if pop email or imap is enabled if not enable one of the two.
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Old 12-29-2010, 09:40 PM   #4
bdrawve
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Posts: 8
Karma: 10
Join Date: Dec 2010
Device: kindle
Pop was enabled, enabled imap and still get this error message:

Email Blink: The Power of Thinking Without Thinking to brdrawve@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (u'smtp.gmail.com', 587)

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 103, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 776, in _get_socket
File "ssl.py", line 342, in wrap_socket
File "ssl.py", line 121, in __init__
File "ssl.py", line 281, in do_handshake
SSLError: [Errno 1] _ssl.c:499: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol

Retrying in 301 seconds...
connect: (u'smtp.gmail.com', 587)
connect: (u'smtp.gmail.com', 587)

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 103, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 776, in _get_socket
File "ssl.py", line 342, in wrap_socket
File "ssl.py", line 121, in __init__
File "ssl.py", line 281, in do_handshake
SSLError: [Errno 1] _ssl.c:499: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
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Old 12-29-2010, 09:49 PM   #5
bdrawve
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Posts: 8
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Device: kindle
Also tried with bitdefender firewalls disabled and still doesn't go through....My internet provider is comcast.

Same error>>.
Email Blink: The Power of Thinking Without Thinking to brdrawve@kindle.com
connect: (u'smtp.gmail.com', 587)
connect: (u'smtp.gmail.com', 587)

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 103, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 776, in _get_socket
File "ssl.py", line 342, in wrap_socket
File "ssl.py", line 121, in __init__
File "ssl.py", line 281, in do_handshake
SSLError: [Errno 1] _ssl.c:499: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol

Retrying in 301 seconds...
connect: (u'smtp.gmail.com', 587)
connect: (u'smtp.gmail.com', 587)

Sending failed...
Traceback (most recent call last):
File "site-packages\calibre\gui2\email.py", line 116, in run
File "site-packages\calibre\gui2\email.py", line 170, in sendmail
File "site-packages\calibre\utils\smtp.py", line 103, in sendmail
File "site-packages\calibre\utils\smtplib.py", line 303, in connect
File "site-packages\calibre\utils\smtplib.py", line 776, in _get_socket
File "ssl.py", line 342, in wrap_socket
File "ssl.py", line 121, in __init__
File "ssl.py", line 281, in do_handshake
SSLError: [Errno 1] _ssl.c:499: error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown protocol
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Old 12-30-2010, 02:22 PM   #6
bdrawve
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Sorry for my ignorance on all of this, but anybody have any ideas what I might be doing wrong in the setup or my internet security or provider???

Thanks
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Old 12-30-2010, 04:09 PM   #7
bdrawve
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Could my problem be that the epub books form ibooks has drm when converting to mobi for kindle?? Is there any way to bypass that?
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Old 01-01-2011, 01:03 PM   #8
bdrawve
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Any other hints??
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Old 01-01-2011, 01:07 PM   #9
kovidgoyal
creator of calibre
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That error indicates the server you are connecting too is misconfigured. Since I doubt gmail is misconfigured, that means the connection is being routed to some non gmail server. The only way that can happen is if your computer is infected by some malware.
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Old 01-04-2011, 05:15 AM   #10
DoctorOhh
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Quote:
Originally Posted by bdrawve View Post
Any other hints??
Here is how another person solved this problem.

Quote:
Originally Posted by tcncalibre View Post
I figured it out by noticing that while the gmail set up asks for your gmail user name and places it in the "send email from" field it DOES NOT put your username in the "username" field. Instead it leaves the username field as just "@gmail.com" Thus you need to add your name before the @gmail.com.

Clearly a simple solution but since you type it in in the set up to begin with you don't expect that you might need to type it in again somewhere.
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Old 01-05-2011, 06:57 AM   #11
frankstewart
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I'm trying to email news from calibre to my kindle via my gmail account. I've enabled POP and IMAP on gmail, ensured that the full gmail address is included in the Calibre username but still get the following error. Any ideas what the problem might be?

Traceback (most recent call last):
File "site-packages\calibre\gui2\wizard\send_email.py", line 111, in test_email_settings
File "site-packages\calibre\utils\smtp.py", line 103, 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 567, in create_connection
error: [Errno 10051] A socket operation was attempted to an unreachable network
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Old 01-05-2011, 07:15 AM   #12
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That error implies that something blocked the calibre connection. Have you checked that your firewall is set to allow the calibre-parallel process to make outbound connections?
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Old 01-05-2011, 10:30 AM   #13
frankstewart
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Thanks - was using my office pc - will try again from the home pc.
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Old 01-09-2011, 03:12 AM   #14
frankstewart
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Thanks - problem solved, it works fine from my home computer so this was evidently a firewall restriction on my office's network.
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