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Old 01-14-2023, 05:27 AM   #1
hywelbane
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Not able to send through Calibre anymore
I was always able to send books by email to my Kindle account, but that stopped working this morning. I get the below error. I can send the book as an attachment from my gmail account without problem. Do I need to set up SMTP and if so is it safe to enter my gmail password in calibre?
Sending failed...

Traceback (most recent call last):
File "calibre\gui2\email.py", line 47, in run
File "calibre\gui2\email.py", line 136, in sendmail
File "calibre\utils\smtp.py", line 162, in sendmail
File "calibre\utils\smtp.py", line 142, in sendmail_direct
OSError: Failed to send mail: SMTPRecipientsRefused({'my account@kindle.com': (550, b'5.7.1 IP address blacklisted by recipient')})
On a side note, since the Kindle switch to EPUB, all my books are sent without cover, even if I change the metadata in Calibre. Is there a way to fix this?

Thank you
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Old 01-14-2023, 05:38 AM   #2
kovidgoyal
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https://manual.calibre-ebook.com/faq...-using-calibre
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Old 01-01-2024, 08:13 AM   #3
Sim
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Unhappy This solution is no longer working.
Quote:
Originally Posted by kovidgoyal View Post
My calibre 'send' to email feature has suddenly stopped working again. I tried:

1) new gmx email before and after disabling firewall
2) old hotmail email after disabling firewall.

Nothing is working. What can I do? I just want to do what I have done for years - email books I download to myself using calibre.
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Old 01-01-2024, 01:03 PM   #4
gbm
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Send by email is working for me.
Please open the jobs button on lower right calibre and post the results of "show jobs details" of the failed email send.


Should look like this:

Spoiler:
Code:
Starting job: Email Bedlam Boyz to XXXXXX@kindle.com 
connect: to ('mail.gmx.com', 587) None 
reply: b'220 gmx.net (mrgmx004) Nemesis ESMTP Service ready\r\n' 
reply: retcode (220); Msg: b'gmx.net (mrgmx004) Nemesis ESMTP Service ready' 
connect: b'gmx.net (mrgmx004) Nemesis ESMTP Service ready' 
send: 'ehlo [127.0.1.1]\r\n' 
reply: b'250-gmx.net Hello [127.0.1.1] [XXX.XX.XXX.XXX]\r\n' 
reply: b'250-8BITMIME\r\n' 
reply: b'250-SIZE 69920427\r\n' 
reply: b'250 STARTTLS\r\n' 
reply: retcode (250); Msg: b'gmx.net Hello [127.0.1.1] [XXX.XX.XXX.XXX]\n8BITMIME\nSIZE 69920427\nSTARTTLS' 
send: 'STARTTLS\r\n' 
reply: b'220 OK\r\n' 
reply: retcode (220); Msg: b'OK' 
send: 'ehlo [127.0.1.1]\r\n' 
reply: b'250-gmx.net Hello [127.0.1.1] [XXX.XX.XXX.XXX]\r\n' 
reply: b'250-8BITMIME\r\n' 
reply: b'250-AUTH LOGIN PLAIN\r\n' 
reply: b'250 SIZE 69920427\r\n' 
reply: retcode (250); Msg: b'gmx.net Hello [127.0.1.1] [XXX.XX.XXX.XXX]\n8BITMIME\nAUTH LOGIN PLAIN\nSIZE 69920427' 
send: AUTH  
reply: b'235 Authentication succeeded\r\n' 
reply: retcode (235); Msg: b'Authentication succeeded' 
send: 'mail FROM: size=408795\r\n' 
reply: b'250 Requested mail action okay, completed\r\n' 
reply: retcode (250); Msg: b'Requested mail action okay, completed' 
send: 'rcpt TO:\r\n' 
reply: b'250 OK\r\n' 
reply: retcode (250); Msg: b'OK' 
send: 'data\r\n' 
reply: b'354 Start mail input; end with .\r\n' 
reply: retcode (354); Msg: b'Start mail input; end with .' 
data: (354, b'Start mail input; end with .') 
send: b'From: xxxx@gmx.com\r\nTo: XXXXXX@kindle.com\r\nSubject: Ye6q8Ij4enUBXpPRLxzI22\r\nD... 
reply: b'250 Requested mail action okay, completed: id=1MUGi9-1rkNXx3XOd-00RGPb\r\n' 
reply: retcode (250); Msg: b'Requested mail action okay, completed: id=1MUGi9-1rkNXx3XOd-00RGPb' 
data: (250, b'Requested mail action okay, completed: id=1MUGi9-1rkNXx3XOd-00RGPb') 
send: 'quit\r\n' 
reply: b'221 gmx.net Service closing transmission channel\r\n' 
reply: retcode (221); Msg: b'gmx.net Service closing transmission channel' 
Email successfully sent


bernie

Quote:
Originally Posted by Sim View Post
My calibre 'send' to email feature has suddenly stopped working again. I tried:

1) new gmx email before and after disabling firewall
2) old hotmail email after disabling firewall.

Nothing is working. What can I do? I just want to do what I have done for years - email books I download to myself using calibre.
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Old 01-05-2024, 04:36 PM   #5
painting-words
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Sorry for highjacking this post, I've just had a similar problem for ages and taking a chance that someone knows how to help me... I've been unable to use the send email to kindle function for ages now.
If that's relevant, I run calibre 5.44 because my Mac iOS is too old... and I have a @hotmail.com address.

Anyway, just in case, here's the error message I got when I tried today:
Spoiler:


calibre, version 5.44.0 (darwin, embedded-python: True)
Failed to email book: Failed: Email NAME OF BOOK to myaccount@kindle.com

Starting job: Email NAME OF BOOK to myaccount@kindle.com
Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: ('smtp-mail.outlook.com', 587)
connect: to ('smtp-mail.outlook.com', 587) None
reply: b'220 YQZPR01CA0089.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 5 Jan 2024 21:18:34 +0000\r\n'
reply: retcode (220); Msg: b'YQZPR01CA0089.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 5 Jan 2024 21:18:34 +0000'
connect: b'YQZPR01CA0089.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 5 Jan 2024 21:18:34 +0000'
send: 'ehlo MacBook-Air-de-myname.local\r\n'
reply: b'250-YQZPR01CA0089.outlook.office365.com Hello [216.137.119.154]\r\n'
reply: b'250-SIZE 157286400\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-DSN\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-BINARYMIME\r\n'
reply: b'250-CHUNKING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'YQZPR01CA0089.outlook.office365.com Hello [216.137.119.154]\nSIZE 157286400\nPIPELINING\nDSN\nENHANCEDSTATUSCODES\nS TARTTLS\n8BITMIME\nBINARYMIME\nCHUNKING\nSMTPUTF8'
send: 'STARTTLS\r\n'
reply: b'220 2.0.0 SMTP server ready\r\n'
reply: retcode (220); Msg: b'2.0.0 SMTP server ready'
send: 'ehlo MacBook-Air-de-myname.local\r\n'
reply: b'250-YQZPR01CA0089.outlook.office365.com Hello [216.137.119.154]\r\n'
reply: b'250-SIZE 157286400\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-DSN\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-AUTH LOGIN XOAUTH2\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-BINARYMIME\r\n'
reply: b'250-CHUNKING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'YQZPR01CA0089.outlook.office365.com Hello [216.137.119.154]\nSIZE 157286400\nPIPELINING\nDSN\nENHANCEDSTATUSCODES\nA UTH LOGIN XOAUTH2\n8BITMIME\nBINARYMIME\nCHUNKING\nSMTPUTF8'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'MjF0b3dsSFRNTDQ=\r\n'
reply: b'535 5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQZPR01CA0089.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:18:46.945Z 08DC0D13B8359358]\r\n'
reply: retcode (535); Msg: b'5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQZPR01CA0089.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:18:46.945Z 08DC0D13B8359358]'

Sending failed...

Traceback (most recent call last):
File "calibre/gui2/email.py", line 48, in run
File "calibre/gui2/email.py", line 137, in sendmail
File "calibre/utils/smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (535, b'5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQZPR01CA0089.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:18:46.945Z 08DC0D13B8359358]')


Retrying in 301 seconds...

Waiting 301 seconds before sending, to avoid being marked as spam.
You can control this delay via Preferences->Tweaks
connect: ('smtp-mail.outlook.com', 587)
connect: to ('smtp-mail.outlook.com', 587) None
reply: b'220 YQBPR01CA0098.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 5 Jan 2024 21:23:47 +0000\r\n'
reply: retcode (220); Msg: b'YQBPR01CA0098.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 5 Jan 2024 21:23:47 +0000'
connect: b'YQBPR01CA0098.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 5 Jan 2024 21:23:47 +0000'
send: 'ehlo MacBook-Air-de-myname.local\r\n'
reply: b'250-YQBPR01CA0098.outlook.office365.com Hello [216.137.119.154]\r\n'
reply: b'250-SIZE 157286400\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-DSN\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-BINARYMIME\r\n'
reply: b'250-CHUNKING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'YQBPR01CA0098.outlook.office365.com Hello [216.137.119.154]\nSIZE 157286400\nPIPELINING\nDSN\nENHANCEDSTATUSCODES\nS TARTTLS\n8BITMIME\nBINARYMIME\nCHUNKING\nSMTPUTF8'
send: 'STARTTLS\r\n'
reply: b'220 2.0.0 SMTP server ready\r\n'
reply: retcode (220); Msg: b'2.0.0 SMTP server ready'
send: 'ehlo MacBook-Air-de-myname.local\r\n'
reply: b'250-YQBPR01CA0098.outlook.office365.com Hello [216.137.119.154]\r\n'
reply: b'250-SIZE 157286400\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-DSN\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-AUTH LOGIN XOAUTH2\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-BINARYMIME\r\n'
reply: b'250-CHUNKING\r\n'
reply: b'250 SMTPUTF8\r\n'
reply: retcode (250); Msg: b'YQBPR01CA0098.outlook.office365.com Hello [216.137.119.154]\nSIZE 157286400\nPIPELINING\nDSN\nENHANCEDSTATUSCODES\nA UTH LOGIN XOAUTH2\n8BITMIME\nBINARYMIME\nCHUNKING\nSMTPUTF8'
send: AUTH <censored>
reply: b'334 UGFzc3dvcmQ6\r\n'
reply: retcode (334); Msg: b'UGFzc3dvcmQ6'
send: 'MjF0b3dsSFRNTDQ=\r\n'
reply: b'535 5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQBPR01CA0098.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:23:59.254Z 08DC0CC9A22E0E4F]\r\n'
reply: retcode (535); Msg: b'5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQBPR01CA0098.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:23:59.254Z 08DC0CC9A22E0E4F]'

Sending failed...

Traceback (most recent call last):
File "calibre/gui2/email.py", line 48, in run
File "calibre/gui2/email.py", line 137, in sendmail
File "calibre/utils/smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (535, b'5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQBPR01CA0098.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:23:59.254Z 08DC0CC9A22E0E4F]')

Job: "Email NAME OF BOOK to myaccount@kindle.com" failed with error:
Traceback (most recent call last):
File "calibre/gui2/threaded_jobs.py", line 82, in start_work
File "calibre/gui2/email.py", line 105, in __call__
File "calibre/gui2/email.py", line 48, in run
File "calibre/gui2/email.py", line 137, in sendmail
File "calibre/utils/smtp.py", line 180, in sendmail
File "smtplib.py", line 734, in login
File "smtplib.py", line 723, in login
File "smtplib.py", line 646, in auth
smtplib.SMTPAuthenticationError: (535, b'5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQBPR01CA0098.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:23:59.254Z 08DC0CC9A22E0E4F]')

Called with args: ('/var/folders/hk/ty5tg4x13xxb3m8yzp9rqbg80000gn/C/calibre_5.44.0_tmp_7z9hrhk5/vnx52qabcaltmpfmt.epub', "NAME OF BOOK.epub", 'myaccount@kindle.com', "E-book: NAME OF BOOK", "Attached, you will find the e-book\n\nNAME OF BOOK\n\tby AUTHOR\n\nin the EPUB format.") {'notifications': <queue.Queue object at 0x1230c2910>, 'abort': <threading.Event object at 0x1230c2e50>, 'log': <calibre.utils.logging.GUILog object at 0x1230c2f10>}


If anyone has any idea what's the issue and can point me to a solution, it would be much appreciated!
Last edited by theducks; 01-05-2024 at 05:36 PM. Reason: spoilered log
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Old 01-05-2024, 06:03 PM   #6
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You've just published your password btw.
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Old 01-05-2024, 11:19 PM   #7
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Quote:
Originally Posted by Sarmat89 View Post
You've just published your password btw.
Does it really matter when the error message is invalid user credentials?

Code:
reply: b'535 5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQZPR01CA0089.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:18:46.945Z 08DC0D13B8359358]\r\n'

reply: retcode (535); Msg: b'5.7.139 Authentication unsuccessful, the user credentials were incorrect. [YQZPR01CA0089.CANPRD01.PROD.OUTLOOK.COM 2024-01-05T21:18:46.945Z 08DC0D13B8359358]'
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Old 01-05-2024, 11:36 PM   #8
kovidgoyal
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Quote:
Originally Posted by Sarmat89 View Post
You've just published your password btw.
No they havent, credentials are censored in the logs

Quote:
send: AUTH <censored>
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Old 01-05-2024, 11:37 PM   #9
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@painting-words: Your username or password are likely incorrect. Make sure the username ends with @hotmail.com and the password is correct.
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